Name: 69361-41-7|(4-Bromobut-1-yn-1-yl)trimethylsilane|95%
Brand: Ambeed
SKU: A355194
Price: 11.0 USD
Availability: InStock
Rating: 91 (28 reviews)

1
[ 2117-12-6 ]
[ 69361-41-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With carbon tetrabromide; triphenylphosphine In diethyl ether at 20℃; for 48h;
96.3%	With carbon tetrabromide; triphenylphosphine In diethyl ether for 48h; Ambient temperature;
89%	With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -20 - 20℃;

87%	With carbon tetrabromide; triphenylphosphine In dichloromethane at -30 - 0℃;
75%	With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -20 - 20℃; for 5h; Inert atmosphere;
75%	With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -20 - 23℃; for 16h; Inert atmosphere;
63%	With pyridine; triphenyl phosphite; bromine In diethyl ether for 8h; Ambient temperature;
32%	With phosphorus tribromide In dichloromethane at 0℃; for 0.25h;
3.418%	With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 5h; Inert atmosphere;
	(i) TsCl, Py, (ii) LiBr, DMF; Multistep reaction;
	With pyridine; p-toluenesulfonyl chloride; lithium bromide 1.) 0 deg C, 1 h, RT, 15 h, 2.) acetone, RT, 13.5 h, then reflux, 6.5 h; Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1: NEt₃ / CH₂Cl₂ / 5 h / 0 - 20 °C 2: 63.0 mmol / LiBr / acetone / 15 h / Heating
	Multi-step reaction with 2 steps 1: 96 percent / pyridine / 10 h / 0 °C 2: 83 percent / LiBr / dimethylformamide / 3 h / 50 °C
	Multi-step reaction with 2 steps 1: Et₃N / CH₂Cl₂ / 2 h, 0 deg C; 3 h, r.t. 2: LiBr / acetone / 15 h / Heating
	Multi-step reaction with 2 steps 1: 93 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h; 2.) rt, 6 h 2: 90 percent / LiBr / acetone / 12 h / 25 °C
	Stage #1: 4-(trimethylsilyl)but-3-yn-1-ol With carbon tetrabromide In dichloromethane at -30℃; for 0.166667h; Stage #2: With triphenylphosphine In dichloromethane at -30 - 0℃;
	With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 5h;
	Multi-step reaction with 2 steps 1: pyridine / 16 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2: lithium bromide / acetone / 36 h / 20 - 56 °C / Schlenk technique; Inert atmosphere; Reflux

Reference： [1]Nishimoto, Yoshihiro; Kajioka, Masayuki; Saito, Takahiro; Yasuda, Makoto; Baba, Akio [Chemical Communications, 2008, # 47, p. 6396 - 6398]
[2]Dobbs, Adrian P.; Jones, Keith; Veal, Ken T. [Tetrahedron, 1998, vol. 54, # 10, p. 2149 - 2160]
[3]Simon, Meike; Karaghiosoff, Konstantin; Knochel, Paul [Organic Letters, 2018, vol. 20, # 12, p. 3518 - 3521]
[4]Dieter, R. Karl; Chen, Ningyi [Journal of Organic Chemistry, 2006, vol. 71, # 15, p. 5674 - 5678]
[5]Wisniewska, Hanna M.; Swift, Elizabeth C.; Jarvo, Elizabeth R. [Journal of the American Chemical Society, 2013, vol. 135, # 24, p. 9083 - 9090]
[6]Lee, Yujin; Rochette, Elise M.; Kim, Junyong; Chen, David Y.-K. [Angewandte Chemie - International Edition, 2017, vol. 56, # 40, p. 12250 - 12254][Angew. Chem., 2017, vol. 129, p. 12418 - 12422]
[7]Clive, Derrick L. J.; Cole, Derek C. [Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3263 - 3270]
[8]Davison, Edwin C.; Forbes, Ian T.; Holmes, Andrew B.; Warner, Jacqueline A. [Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624]
[9]Li, Lin; Zhang, Cheng-Wu; Ge, Jingyan; Qian, Linghui; Chai, Bing-Han; Zhu, Qing; Lee, Jun-Seok; Lim, Kah-Leong; Yao, Shao Q. [Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10821 - 10825][Angew. Chem., 2015, vol. 127, p. 10971 - 10975,5]
[10]Hammoud,A.; Descoins,C. [Bulletin de la Societe Chimique de France, 1978, vol. <II>, p. 299 - 303]
[11]Rossi; Carpita; Ciofalo; Lippolis [Tetrahedron, 1991, vol. 47, # 39, p. 8443 - 8460]
[12]Dickner, Tim; Laschat, Sabine [Advanced Synthesis and Catalysis, 2000, vol. 342, # 8, p. 804 - 811]
[13]Davison, Edwin C.; Forbes, Ian T.; Holmes, Andrew B.; Warner, Jacqueline A. [Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624]
[14]Balme, Genevieve; Bouyssi, Didier [Tetrahedron, 1991, vol. 50, # 2, p. 403 - 414]
[15]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[16]Palais, Laetitia; Alexakis, Alexandre [Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10473 - 10485]
[17]Mao, Bin; Fañanás-Mastral, Martín; Lutz, Martin; Feringa, Ben L. [Chemistry - A European Journal, 2013, vol. 19, # 2, p. 761 - 770]
[18]Davies, Jonathan A.; Bull, Freya M.; Walker, Paul D.; Weir, Angus N. M.; Lavigne, Rob; Masschelein, Joleen; Simpson, Thomas J.; Race, Paul R.; Crump, Matthew P.; Willis, Christine L. [Organic Letters, 2020, vol. 22, # 16, p. 6349 - 6353]

2
[ 75-77-4 ]
[ 38771-21-0 ]
[ 69361-41-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 4-bromobut-1-yne With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
	With n-butyllithium Multistep reaction;
	With n-butyllithium 1) THF, n-hexane, -70 deg C, 4 h, 2) room temperature, 20 h; Yield given. Multistep reaction;

Reference： [1]Sibbersen, Christian; Palmfeldt, Johan; Hansen, Jakob; Gregersen, Niels; Jorgensen, Karl Anker; Johannsen, Mogens [Chemical Communications, 2013, vol. 49, # 38, p. 4012 - 4014]
[2]Negishi, Ei-ichi; Valente, Louis F.; Kobayashi, Makoto [Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3298 - 3299]
[3]Gleiter, Rolf; Fischer, Evelyn [Chemische Berichte, 1992, vol. 125, # 8, p. 1899 - 1912]

3
[ 71570-25-7 ]
[ 69361-41-7 ]
[ 72039-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium; zinc(II) chloride 1.) THF, reflux, 3-4 h, 2.) THF, room temperature, 3-6 h; Yield given. Multistep reaction;

Reference： [1]Negishi, Ei-ichi; Valente, Louis F.; Kobayashi, Makoto [Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3298 - 3299]

4
[ 5323-87-5 ]
[ 69361-41-7 ]
[ 141462-71-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran for 1h; Reflux; Inert atmosphere; Stage #2: 3-Ethoxycyclohex-2-en-1-one In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
70%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran; ethylene dibromide for 2h; Reflux; Stage #2: 3-Ethoxycyclohex-2-en-1-one In tetrahydrofuran; ethylene dibromide at 0 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethylene dibromide
	With magnesium 1) THF, room temperature, 2) THF, room temperature, 3 h; Yield given. Multistep reaction;

	With magnesium 1.) THF, 1 h, 2.) 20 deg C, 14 h; Yield given. Multistep reaction;
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In diethyl ether at 20℃; Stage #2: 3-Ethoxycyclohex-2-en-1-one In tetrahydrofuran; diethyl ether at 0 - 20℃;

Reference： [1]Huang, Jun; Qu, Yongzheng; Wang, Zheyuan; Yang, Zhen; Zhang, Wendou; Zhang, Zhongchao [Journal of the American Chemical Society, 2020, vol. 142, # 14, p. 6511 - 6515]
[2]Location in patent: experimental part Lutteke, Ginger; Alhussainy, Rana; Wrigstedt, Pauli J.; Hue, B. T. Buu; De Gelder, Rene; Van Maarseveen, Jan H.; Hiemstra, Henk [European Journal of Organic Chemistry, 2008, # 5, p. 925 - 933]
[3]Gleiter, Rolf; Fischer, Evelyn [Chemische Berichte, 1992, vol. 125, # 8, p. 1899 - 1912]
[4]Fox, Martin E.; Holmes, Andrew B.; Forbes, Ian T.; Thompson, Mervyn [Journal of the Chemical Society. Perkin transactions I, 1994, # 23, p. 3379 - 3396]
[5]Palais, Laetitia; Alexakis, Alexandre [Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10473 - 10485]

5
[ 69361-41-7 ]
[ 75-24-1 ]
[ 86994-12-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With zirconocene dichloride In dichloromethane at 25℃;
92 % Chromat.	With zirconocene dichloride In dichloromethane at 25℃; for 24h;
	With zirconocene dichloride

Reference： [1]Negishi, Ei-ichi; Boardman, Larry D.; Tour, James M.; Sawada, Hiroyuki; Rand, Cynthia L. [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6344 - 6346]
[2]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[3]Boardman, Larry D.; Bagheri, Vahid; Sawad, Hiroyuki; Negishi, Ei-ichi [Journal of the American Chemical Society, 1984, vol. 106, # 20, p. 6105 - 6107]

6
[ 69361-41-7 ]
[ 18925-10-5 ]
2-(2-propen-1-yl)-1-(trimethylsilyl)cyclobutene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In tetrahydrofuran at 60℃; for 24h;
84%

Reference： [1]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[2]Boardman, Larry D.; Bagheri, Vahid; Sawad, Hiroyuki; Negishi, Ei-ichi [Journal of the American Chemical Society, 1984, vol. 106, # 20, p. 6105 - 6107]

7
[ 69361-41-7 ]
[ 74133-09-8 ]
Trimethyl-[(E)-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-oct-5-en-1-ynyl]-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium; zinc(II) chloride 1.) THF, reflux, 3-4 h, 2.) THF, room temperature, 3-6 h; Multistep reaction;

Reference： [1]Negishi, Ei-ichi; Valente, Louis F.; Kobayashi, Makoto [Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3298 - 3299]

8
[ 69361-41-7 ]
[ 74133-10-1 ]
[(5E,9E)-6,10-Dimethyl-12-(2,6,6-trimethyl-cyclohex-1-enyl)-dodeca-5,9-dien-1-ynyl]-trimethyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium; zinc(II) chloride 1.) THF, reflux, 3-4 h, 2.) THF, room temperature, 3-6 h; Multistep reaction;

Reference： [1]Negishi, Ei-ichi; Valente, Louis F.; Kobayashi, Makoto [Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3298 - 3299]

9
[ 69361-41-7 ]
[ 86994-13-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With diisobutylaluminium hydride In diethyl ether at 40℃; for 2h;
	With diisobutylaluminium hydride In diethyl ether at 25℃;

Reference： [1]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[2]Negishi, Ei-ichi; Boardman, Larry D.; Tour, James M.; Sawada, Hiroyuki; Rand, Cynthia L. [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6344 - 6346]

10
[ 69361-41-7 ]
[ 83094-06-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With diisobutylaluminium hydride In benzene at 25℃; for 2h;
	With Schwartz's reagent; aluminium trichloride 1.) benzene, 25 deg C, 12 h; 2.) CH₂Cl₂, 0 deg C, 1 h; Yield given. Multistep reaction;
	With zirconocene dichloride; diisobutylaluminium hydride

	Multi-step reaction with 2 steps 1: 1.) DIBAH, 2.) I₂ / 1.) ether, 40 deg C, 2 h; 2.) ether, THF, -78 deg C 2: 81 percent Chromat_. / t-BuLi / diethyl ether; pentane / 1.) -78 deg C, 30 min; 2.) warm slowly up to 25 deg C
	Multi-step reaction with 2 steps 1: 1.) i-Bu₂AlH, 2.) I₂ / 1.) Et₂O 2: 81 percent / t-BuLi / diethyl ether / -78 -> 25 deg C

Reference： [1]Negishi, Ei-ichi; Boardman, Larry D.; Tour, James M.; Sawada, Hiroyuki; Rand, Cynthia L. [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6344 - 6346]
[2]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[3]Boardman, Larry D.; Bagheri, Vahid; Sawad, Hiroyuki; Negishi, Ei-ichi [Journal of the American Chemical Society, 1984, vol. 106, # 20, p. 6105 - 6107]
[4]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[5]Negishi, Ei-ichi; Boardman, Larry D.; Tour, James M.; Sawada, Hiroyuki; Rand, Cynthia L. [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6344 - 6346]

11
[ 69361-41-7 ]
[ 86994-20-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With diisobutylaluminium hydride In tetrahydrofuran; diethyl ether at 40℃; for 12h; Stage #2: With iodine In tetrahydrofuran; diethyl ether at -70 - 0℃;
	With iodine; diisobutylaluminium hydride 1.) Et₂O; Multistep reaction;
	With iodine; diisobutylaluminium hydride 1.) ether, 40 deg C, 2 h; 2.) ether, THF, -78 deg C; Yield given. Multistep reaction;

Reference： [1]Dieter, R. Karl; Chen, Ningyi [Journal of Organic Chemistry, 2006, vol. 71, # 15, p. 5674 - 5678]
[2]Negishi, Ei-ichi; Boardman, Larry D.; Tour, James M.; Sawada, Hiroyuki; Rand, Cynthia L. [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6344 - 6346]
[3]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]

12
[ 86994-11-8 ]
[ 69361-41-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With lithium bromide In acetone Heating;
90%	With lithium bromide In acetone at 25℃; for 12h;
86%	With tetra-(n-butyl)ammonium iodide; lithium bromide In acetone at 20℃; for 36h;

83%	With lithium bromide In N,N-dimethyl-formamide at 50℃; for 3h;
69%	With lithium bromide In acetone at 20℃;
8.8 g	With lithium bromide In acetone at 20℃;
	With lithium bromide In acetone at 20℃; for 5h;	5 4-Bromobut-1-ynyl)trimethylsilane (22); [00157] Crude toluene-4-sulfonic acid 4-trimethylsilanyl-but-3-ynyl ester is dissolved in dry acetone containing LiBr and the reaction mixture is stirred at room temperature for 5h. The reaction mixture is poured into water, extracted with ethylacetate, the organic layer is washed with brine, dried over Na2SO4, concentrated and distilled under reduced pressure (75-80°C/20Torr) to give 4-bromobut-1- ynyl)trimethylsilane as a colorless oil.1H-NMR (400 MHz1 CDCI3); δ (ppm): 0.11 (s, 9H)1 2.58 (t, J=7.1 Hz1 2H)1 4.09 (t, J=7.1Hz1 2H)
	With lithium bromide In acetone at 20 - 56℃; for 36h; Schlenk technique; Inert atmosphere; Reflux;

Reference： [1]Dower, William V.; Vollhardt, K. Peter C. [Tetrahedron, 1986, vol. 42, # 6, p. 1873 - 1882]
[2]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]
[3]Leitner, Christian; Gaich, Tanja [Chemical Communications, 2017, vol. 53, # 54, p. 7451 - 7453]
[4]Davison, Edwin C.; Forbes, Ian T.; Holmes, Andrew B.; Warner, Jacqueline A. [Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624]
[5]Li, Xiang David; Li, Xin; Yang, Tangpo [RSC Advances, 2020, vol. 10, # 69, p. 42076 - 42083]
[6]Bian, Jianwei; Van Wingerden, Matthew; Ready, Joseph M. [Journal of the American Chemical Society, 2006, vol. 128, # 23, p. 7428 - 7429]
[7]Current Patent Assignee: MERZ GMBH & CO. KGAA - WO2010/63487, 2010, A1 Location in patent: Page/Page column 75
[8]Davies, Jonathan A.; Bull, Freya M.; Walker, Paul D.; Weir, Angus N. M.; Lavigne, Rob; Masschelein, Joleen; Simpson, Thomas J.; Race, Paul R.; Crump, Matthew P.; Willis, Christine L. [Organic Letters, 2020, vol. 22, # 16, p. 6349 - 6353]

13
4-(trimethylsilyl)but-3-ynyl methanesulfonate [ No CAS ]
[ 69361-41-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium bromide In acetone for 15h; Heating; Yield given;
63.0 mmol	With lithium bromide In acetone for 15h; Heating;
6.4 g	With lithium bromide In acetone at 20℃; for 19h;

Reference： [1]Balme, Genevieve; Bouyssi, Didier [Tetrahedron, 1991, vol. 50, # 2, p. 403 - 414]
[2]Dickner, Tim; Laschat, Sabine [Advanced Synthesis and Catalysis, 2000, vol. 342, # 8, p. 804 - 811]
[3]Location in patent: experimental part Lutteke, Ginger; Alhussainy, Rana; Wrigstedt, Pauli J.; Hue, B. T. Buu; De Gelder, Rene; Van Maarseveen, Jan H.; Hiemstra, Henk [European Journal of Organic Chemistry, 2008, # 5, p. 925 - 933]

14
[ 69361-41-7 ]
[ 139409-34-0 ]
[ 169384-05-8 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium carbonate In acetone Heating;
59%	With potassium carbonate In acetone for 24h; Heating;

Reference： [1]Dobbs, Adrian P. [Tetrahedron Letters, 1995, vol. 36, # 27, p. 4857 - 4860]
[2]Dobbs, Adrian P.; Jones, Keith; Veal, Ken T. [Tetrahedron, 1998, vol. 54, # 10, p. 2149 - 2160]

15
[ 69361-41-7 ]
[ 132974-85-7 ]
[ 229160-60-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: With magnesium In tetrahydrofuran Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 0.166667h; Stage #3: 4-bromo-1-trimethylsilylbut-1-yne; (-)-(5S)-5-[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one With chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 0.25h;

Reference： [1]Cossy, Janine; Cases, Manuel; Pardo, Domingo Gomez [Tetrahedron, 1999, vol. 55, # 19, p. 6153 - 6166]

16
[ 69361-41-7 ]
4-bromo-1-iodo-1-trimethylsilyl-1-butene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With diisobutylaluminium hydride In diethyl ether at 40℃; for 2h; Stage #2: With iodine In tetrahydrofuran; diethyl ether at -78 - 0℃;

Reference： [1]Dickner, Tim; Laschat, Sabine [Advanced Synthesis and Catalysis, 2000, vol. 342, # 8, p. 804 - 811]

17
[ 69361-41-7 ]
[ 183376-52-5 ]
[ 283158-09-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; zinc dibromide In tetrahydrofuran at 50℃; for 12h; Stage #2: (Z)-1,4-diiodo-2-methyl-1-butene With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In tetrahydrofuran at 23℃; for 12h; Further stages.;

Reference： [1]Negishi, Ei-Ichi; Liou, Show-Yee; Xu, Caiding; Huo, Shouquan [Organic Letters, 2002, vol. 4, # 2, p. 261 - 264]

18
[ 69361-41-7 ]
[ 107428-17-1 ]
[ 851315-34-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: dimethyl propargylmalonate With sodium hydride In tetrahydrofuran at 0℃; Stage #2: 4-bromo-1-trimethylsilylbut-1-yne at 20℃; for 24h;

Reference： [1]Trost, Barry M.; Rudd, Michael T. [Journal of the American Chemical Society, 2005, vol. 127, # 13, p. 4763 - 4776]

19
[ 827575-53-1 ]
[ 69361-41-7 ]
[ 827575-28-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran for 1.16667h; Stage #2: 6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -15 - 20℃; for 22h;

Reference： [1]Harrison, Tyler J.; Dake, Gregory R. [Organic Letters, 2004, vol. 6, # 26, p. 5023 - 5026]

20
[ 69361-41-7 ]
[ 85908-96-9 ]
2-oxo-4-(4-trimethylsilanyl-but-3-ynyl)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran Stage #2: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -15 - 20℃;

Reference： [1]Harrison, Tyler J.; Dake, Gregory R. [Organic Letters, 2004, vol. 6, # 26, p. 5023 - 5026]

21
[ 69361-41-7 ]
[ 475051-33-3 ]
[ 475051-26-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 1h; Stage #2: 1,4-dioxaspiro[4.5]dec-8-en-7-yl pivalate In toluene at 20℃; for 15h; Stage #3: With potassium carbonate In methanol at 20℃; for 4h; Further stages.;

Reference： [1]Zhang, Liming; Koreeda, Masato [Organic Letters, 2002, vol. 4, # 21, p. 3755 - 3758]

22
[ 69361-41-7 ]
(2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide [ No CAS ]
(6-(1,3-dioxolan-2-yl)hex-1-ynyl)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;
61%	With n-butylzinc bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;
61%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; n-butylzinc bromide; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;

Reference： [1]O'Brien, Christopher J.; Kantchev, Eric Assen B.; Chass, Gregory A.; Hadei, Niloufar; Hopkinson, Alan C.; Organ, Michael G.; Setiadi, David H.; Tang, Ting-Hua; Fang, De-Cai [Tetrahedron, 2005, vol. 61, # 41, p. 9723 - 9735]
[2]Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Organ, Michael G. [Organic Letters, 2005, vol. 7, # 17, p. 3805 - 3807]
[3]Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Organ, Michael G. [Journal of Organic Chemistry, 2005, vol. 70, # 21, p. 8503 - 8507]

23
[ 69361-41-7 ]
[ 271769-81-4 ]
[ 870776-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; dimethyl amine; zinc at 80℃; for 3h; Stage #2: (1,1-dimethylethyl)[(2-iodophenyl)methoxy]dimethylsilane With dimethyl amine at 80℃; for 1h;

Reference： [1]Mukai, Chisato; Hirose, Toshiyuki; Teramoto, Satoshi; Kitagaki, Shinji [Tetrahedron, 2005, vol. 61, # 46, p. 10983 - 10994]

24
[ 67826-81-7 ]
[ 69361-41-7 ]
trimethyl-tetradeca-1,5-diynyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Heating; Stage #2: With copper(I) bromide In tetrahydrofuran at -45℃; for 0.333333h; Stage #3: iododecyne In tetrahydrofuran at -40℃; for 0.5h;

Reference： [1]Sun, Jianwei; Kozmin, Sergey A. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13512 - 13513]

25
[ 868701-16-0 ]
[ 69361-41-7 ]
8-triisopropylsilanyloxy-1-trimethylsilanyl-octa-1,5-diyne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Heating; Stage #2: With copper(I) bromide In tetrahydrofuran at -45℃; for 0.333333h; Stage #3: (4-iodo-but-3-ynyloxy)-triisopropyl-silane In tetrahydrofuran at -40℃; for 0.5h;

Reference： [1]Sun, Jianwei; Kozmin, Sergey A. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13512 - 13513]

26
[ 69361-41-7 ]
[ 861344-74-3 ]
trimethyl-(8-phenyl-octa-1,5-diynyl)-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Heating; Stage #2: With copper(I) bromide In tetrahydrofuran at -45℃; for 0.333333h; Stage #3: (4-iodobut-3-yn-1-yl)benzene In tetrahydrofuran at -40℃; for 0.5h;

Reference： [1]Sun, Jianwei; Kozmin, Sergey A. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13512 - 13513]

27
[ 69361-41-7 ]
[ 130248-71-4 ]
trimethyl-(9-phenyl-nona-1,5-diynyl)-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Heating; Stage #2: With copper(I) bromide In tetrahydrofuran at -45℃; for 0.333333h; Stage #3: 1-iodo-5-phenyl-1-pentyne In tetrahydrofuran at -40℃; for 0.5h;

Reference： [1]Sun, Jianwei; Kozmin, Sergey A. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13512 - 13513]

28
[ 897960-51-9 ]
[ 69361-41-7 ]
[ 897960-55-3 ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran at 0℃; for 1h; Stage #2: 6-allyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran at 20℃; for 12h;

Reference： [1]Harrison, Tyler J.; Kozak, Jennifer A.; Corbella-Pane, Montserrat; Dake, Gregory R. [Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4525 - 4529]

29
[ 69361-41-7 ]
(E)-3-iodo-2-methyl-prop-2-en-1-ol [ No CAS ]
[ 257885-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; zinc dibromide In tetrahydrofuran at 55℃; for 6h; Stage #2: (E)-3-iodo-2-methyl-prop-2-en-1-ol With ethylzinc bromide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h;

Reference： [1]Tan, Ze; Negishi, Ei-Ichi [Organic Letters, 2006, vol. 8, # 13, p. 2783 - 2785]

30
[ 69361-41-7 ]
[ 85909-08-6 ]
[ 897960-52-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With magnesium In tetrahydrofuran at 20℃; for 18h;

Reference： [1]Harrison, Tyler J.; Kozak, Jennifer A.; Corbella-Pane, Montserrat; Dake, Gregory R. [Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4525 - 4529]

31
[ 69361-41-7 ]
[ 85908-96-9 ]
[ 897960-48-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran for 0.75h; Stage #2: 2-oxopiperidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran at -78 - 20℃; for 2h;

Reference： [1]Harrison, Tyler J.; Kozak, Jennifer A.; Corbella-Pane, Montserrat; Dake, Gregory R. [Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4525 - 4529]

32
[ 917879-06-2 ]
[ 75-77-4 ]
[ 69361-41-7 ]
[ 917879-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In diethyl ether at 10 - 20℃; Stage #2: 2-(4-methoxybenzyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester; chloro-trimethyl-silane With copper(I) bromide dimethylsulfide complex; triethylamine In tetrahydrofuran Stage #3: In tetrahydrofuran; diethyl ether at -78 - -45℃;

Reference： [1]Gotchev, Dimitar B.; Comins, Daniel L. [Journal of Organic Chemistry, 2006, vol. 71, # 25, p. 9393 - 9402]

33
[ 69361-41-7 ]
[ 67781-10-6 ]

Yield	Reaction Conditions	Operation in experiment
97.79%	With copper (I) iodide; magnesium In tetrahydrofuran at 0 - 20℃; for 2h;	1.1 Example 1 1. Add 415mg (2.17mmol) of cuprous iodide and 57mg (2.39mmol) of magnesium scraps into the there-necked flask, and add 2mL of dry tetrahydrofuran, warm to 0°C under stirring, then slowly add 500mg (2.17mmol) of formula 1. (4-bromo-1-butyne)-trimethylsilane was shown. After the addition was completed, the temperature was gradually raised to room temperature. The reaction was stirred at room temperature for 2 hours to complete the reaction. The reaction was quenched with 110 mg (0.44 mmol) of iodine. Extraction with methyl chloride, and the organic phase was spin-dried to obtain 458.96 mg (2.12 mmol) of the compound of formula 2 with a yield of 91.79%.
	With magnesium In tetrahydrofuran at 40℃; for 0.5h;
	With magnesium; ethylene dibromide In tetrahydrofuran for 2h; Inert atmosphere; Reflux;

Reference： [1]Current Patent Assignee: XIAN CONFLUORE BIOLOGICAL TECH - CN113999104, 2022, A Location in patent: Paragraph 0018-0020
[2]Smith, Catherine J; Holmes, Andrew B; Press, Neil J [Chemical Communications, 2002, # 11, p. 1214 - 1215]
[3]Location in patent: experimental part Prakash, Chandran; Rajeshwaran, Ganesan Gobi; Mohanakrishnan, Arasambattu K. [Synthetic Communications, 2010, vol. 40, # 14, p. 2097 - 2107]

34
[ 927384-82-5 ]
[ 69361-41-7 ]
[ 927384-83-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Heating; Stage #2: 6-(<i>tert</i>-butyl-dimethyl-silanyloxy)-heptanoic acid methoxy-methyl-amide In tetrahydrofuran at 0℃; for 0.5h;

Reference： [1]Inui, Masaharu; Nakazaki, Atsuo; Kobayashi, Susumu [Organic Letters, 2007, vol. 9, # 3, p. 469 - 472]

35
[ 69361-41-7 ]
[ 365414-63-7 ]
[ 927384-84-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Heating; Stage #2: 6-(O-tert-butyldimethylsilyl)hexanoic acid N-methoxy-N-methylamide In tetrahydrofuran at 0℃; for 0.5h;

Reference： [1]Inui, Masaharu; Nakazaki, Atsuo; Kobayashi, Susumu [Organic Letters, 2007, vol. 9, # 3, p. 469 - 472]

36
[ 69361-41-7 ]
(2S,6R,7S,8S,1'R)-(1"Z)-2-(5'-trimethylsilyl-1'-hydroxypent-4'-ynyl)-7-(4''-trimethylsilyl-but-1''-en-3''-yn-1''-yl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Mg / tetrahydrofuran / 0.5 h / 40 °C 2: 33 percent / tetrahydrofuran / 0.08 h / 25 °C

Reference： [1]Smith, Catherine J; Holmes, Andrew B; Press, Neil J [Chemical Communications, 2002, # 11, p. 1214 - 1215]

37
[ 69361-41-7 ]
(2S,6R,7S,8S,1'S)-(1"Z)-2-(5'-trimethylsilyl-1'-hydroxypent-4'-ynyl)-7-(4''-trimethylsilyl-but-1''-en-3''-yn-1''-yl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Mg / tetrahydrofuran / 0.5 h / 40 °C 2: 60 percent / tetrahydrofuran / 0.08 h / 25 °C

Reference： [1]Smith, Catherine J; Holmes, Andrew B; Press, Neil J [Chemical Communications, 2002, # 11, p. 1214 - 1215]

38
[ 69361-41-7 ]
(5Z)-6-methyl-1-trimethylsilyl-1,2,5-octatriene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg; ZnBr₂ / tetrahydrofuran / 12 h / 50 °C 1.2: 84 percent / Cl₂Pd(dppf)(CH₂Cl₂) / tetrahydrofuran / 12 h / 23 °C 2.1: 40 percent / n-BuLi / diethyl ether / -78 - 23 °C

Reference： [1]Negishi, Ei-Ichi; Liou, Show-Yee; Xu, Caiding; Huo, Shouquan [Organic Letters, 2002, vol. 4, # 2, p. 261 - 264]

39
[ 69361-41-7 ]
[ 32775-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg; ZnBr₂ / tetrahydrofuran / 12 h / 50 °C 1.2: 84 percent / Cl₂Pd(dppf)(CH₂Cl₂) / tetrahydrofuran / 12 h / 23 °C 2.1: 100 percent / t-BuLi / diethyl ether / 45 h / -78 °C
	Multi-step reaction with 2 steps 1.1: Mg; ZnBr₂ / tetrahydrofuran / 12 h / 50 °C 1.2: 84 percent / Cl₂Pd(dppf)(CH₂Cl₂) / tetrahydrofuran / 12 h / 23 °C 2.1: 51 percent / n-BuLi / diethyl ether / -78 - 23 °C

Reference： [1]Negishi, Ei-Ichi; Liou, Show-Yee; Xu, Caiding; Huo, Shouquan [Organic Letters, 2002, vol. 4, # 2, p. 261 - 264]
[2]Negishi, Ei-Ichi; Liou, Show-Yee; Xu, Caiding; Huo, Shouquan [Organic Letters, 2002, vol. 4, # 2, p. 261 - 264]

40
[ 69361-41-7 ]
[ 92143-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: DIBAL / diethyl ether / 2 h / 40 °C 1.2: 62 percent / I₂ / tetrahydrofuran; diethyl ether / -78 - 0 °C 2.1: tBuLi / diethyl ether; pentane / 2 h / -78 °C 2.2: 50 percent / diethyl ether; pentane / 2 h / -78 - 20 °C
	Multi-step reaction with 2 steps 1: 1.) DIBAH, 2.) I₂ / 1.) ether, 40 deg C, 2 h; 2.) ether, THF, -78 deg C 2: 76 percent / 1.) t-BuLi / diethyl ether; pentane / 1.) -78 deg C, 2h; 2.) 25 deg C, 2 h

Reference： [1]Dickner, Tim; Laschat, Sabine [Advanced Synthesis and Catalysis, 2000, vol. 342, # 8, p. 804 - 811]
[2]Negishi,E.; Boardman,L.D.; Sawada,H. [Journal of the American Chemical Society, 1988, vol. 110, p. 5383]

41
[ 69361-41-7 ]
[ 167303-65-3 ]
[ 612062-75-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With hydrogenchloride; iodine; magnesium In tetrahydrofuran; ethyl acetate	5 Step 2:1 -cyclopentyl-5-trimethylsilanyl-pent-4-yn-1-one: Step 2:1 -cyclopentyl-5-trimethylsilanyl-pent-4-yn-1-one: To a solution of (4-bromobut-1-ynyl)trimethylsilane (8.0 g, 39 mmol), from Step 1, in THF (50 mL) was added magnesium turnings (1.14 g, 47 mmol), and iodine (10 mg). The reaction was stirred for one hour at 24° C., and then warmed in an oil bath at 50° C. for one hour, then allowed to cool to 24° C. To the solution, cyclopentanecarboxylic acid methoxy-methyl-amide (6.12 g, 39 mmol) in THF (30 mL) was added. After the reaction was stirred for 4 hours, 2 N HCl (50 mL) and EtOAc (50 mL) were added. The layers were separated, and the aqueous layer was extracted three times with 25 mL of EtOAc. The organic layers were combined and washed successively with 50 mL saturated sodium bicarbonate, 50 mL water, and 40 mL saturated NaCl. The organic layer was then dried with sodium sulfate. After filtering, the organic layer was concentrated using rotary evaporation, and then chromatographed (80 g Si, 3% EtOAc in hexanes) to yield the product (4.39 g, 51% yield). 1H NMR (CDCl3): δ 0.13 (s, 9H), 1.70 (m, 8H), 2.49 (t, J=8.10 Hz, 2H), 2.69 (t, J=7.91 Hz, 2H), 2.88 (p, J=7.91 Hz, 1H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/195239, 2003, A1

42
[ 75-77-4 ]
[ 38019-50-0 ]
[ 69361-41-7 ]
[ 1032475-84-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Heating; Stage #2: With copper(l) iodide In tetrahydrofuran at -78℃; for 0.5h; Stage #3: chloro-trimethyl-silane; 2-allyl-cyclohex-2-enone With triethylamine In tetrahydrofuran at -78 - 20℃; for 12h;

Reference： [1]Location in patent: experimental part Prakash, Chandran; Mohanakrishnan, Arasambattu K. [European Journal of Organic Chemistry, 2008, # 9, p. 1535 - 1543]

43
[ 75-77-4 ]
[ 17605-08-2 ]
[ 69361-41-7 ]
[ 1032476-06-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Heating; Stage #2: With copper(l) iodide In tetrahydrofuran at -78℃; for 0.5h; Stage #3: chloro-trimethyl-silane; 2-allyl-3-methyl-2-cyclohexen-1-one With triethylamine In tetrahydrofuran at -78 - 20℃; for 12h;

Reference： [1]Location in patent: experimental part Prakash, Chandran; Mohanakrishnan, Arasambattu K. [European Journal of Organic Chemistry, 2008, # 9, p. 1535 - 1543]

44
[ 37567-78-5 ]
[ 69361-41-7 ]
[ 1032475-83-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: 1,5-dimethoxy-1,4-cyclohexadiene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 4-bromo-1-trimethylsilylbut-1-yne With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78 - 20℃; for 2h;
	Stage #1: 1,5-dimethoxy-1,4-cyclohexadiene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #3: 4-bromo-1-trimethylsilylbut-1-yne In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Prakash, Chandran; Mohanakrishnan, Arasambattu K. [European Journal of Organic Chemistry, 2008, # 9, p. 1535 - 1543]
[2]Huang, Jun; Qu, Yongzheng; Wang, Zheyuan; Yang, Zhen; Zhang, Wendou; Zhang, Zhongchao [Journal of the American Chemical Society, 2020, vol. 142, # 14, p. 6511 - 6515]

45
[ 69361-41-7 ]
(S)-benzyl glycidyl ether [ No CAS ]
[ 1146630-90-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: (S)-benzyl glycidyl ether With copper(l) iodide In tetrahydrofuran at -40 - -10℃; for 1h; Inert atmosphere; optical yield given as %ee;

Reference： [1]Sommer, Stefan; Kuehn, Marc; Waldmann, Herbert [Advanced Synthesis and Catalysis, 2008, vol. 350, # 11-12, p. 1736 - 1750]

46
[ 69361-41-7 ]
[ 64491-68-5 ]
[ 1146630-89-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: (2S)-2-(methoxymethyl)oxirane With copper(l) iodide In tetrahydrofuran at -40 - -10℃; for 1h; Inert atmosphere;

Reference： [1]Sommer, Stefan; Kuehn, Marc; Waldmann, Herbert [Advanced Synthesis and Catalysis, 2008, vol. 350, # 11-12, p. 1736 - 1750]

47
[ 69361-41-7 ]
C₇H₁₅BrSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With diisobutylaluminium hydride In diethyl ether at 20 - 40℃; Stage #2: With hydrogenchloride; water In diethyl ether at 0℃;

Reference： [1]Nishimoto, Yoshihiro; Kajioka, Masayuki; Saito, Takahiro; Yasuda, Makoto; Baba, Akio [Chemical Communications, 2008, # 47, p. 6396 - 6398]

48
[ 1228351-60-7 ]
[ 69361-41-7 ]
[ 1228351-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium; ethylene dibromide In tetrahydrofuran at 20℃; Heating; Stage #2: With zinc dibromide In tetrahydrofuran at -10 - 0℃; Stage #3: trifluoro-methanesulfonic acid 2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl ester In tetrahydrofuran at -20 - 20℃; for 5.5h; Inert atmosphere;	5 5-Trimethylsilanyl-butyn-3-yl-zinc (24)[00158] To a flame-dried two-necked flask, Mg turnings were added. The flask is gently heated with a heating gun while stirring for 2 minutes. A solution of iodine in THF followed by Br(CH2)2Br is added. A solution of 4-bromobut-1-ynyl)trimethylsilane in THF is slowly added via a syringe over 1 h. Short heating is done with a heating gun, generating a slightly yellow clear solution which is stirred at r.t. for 2 h. The Grignard solution is then transferred via a cannula needle to a flask containing a solution of ZnBr2 in THF at -10 0C. The white creamy suspension is stirred at 0 0C for 1 h. The crude product is used in the next step without further purification. 2-Methyl-5-(4-trimethylsilanyl-but-3-ynyl)-pyrazolo[1,5-a]pyrimidine (28a)[00161] To a solution of trifluoro-methanesulfonic acid 2-methyl-pyrazolo[1 ,5- a]pyrimidin-5-yl ester in dry THF and PdCI2(dppf) (3,8 mol%) at -200C under an argon atmosphere, zinc reagent 5-trimethylsilanyl-butyn-3-yl-zinc is added; the reaction mixture is stirred at -200C for 30 minutes, then at r.t. for 5h; diluted with water, extracted with ethylacetate, the organic layer is washed with brine, dried over Na2SO4, and concentrated. The desired compound is obtained after chromatography on silica (1 :1ethyl acetate/hexanes as eluent).1H-NMR (400 MHz, CDCI3); δ (ppm): 0.11 (s, 9H), 2.48 (s, 3H), 2.68 (t, J=4.3 Hz, 2H), 2.99 (t, J=4.3 Hz, 2H), 6.34 (s, 1 H), 6.63 (d, J=7.1 Hz, 1 H), 8.42 (d, J=7.1 Hz, 1 H). m/z (APCI+) 258 (M+H+)

Reference： [1]Current Patent Assignee: MERZ GMBH & CO. KGAA - WO2010/63487, 2010, A1 Location in patent: Page/Page column 75-76

49
[ 5650-67-9 ]
[ 69361-41-7 ]
C₁₄H₂₂O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran; ethylene dibromide at 20℃; for 3h; Inert atmosphere; Stage #2: With copper(I) bromide dimethylsulfide complex; dimethylsulfide In tetrahydrofuran at -10 - 20℃; Inert atmosphere; Stage #3: 3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one In tetrahydrofuran at -10℃; for 4h; Inert atmosphere;

Reference： [1]Tucker, Joseph W.; Nguyen, John D.; Narayanam, Jagan M. R.; Krabbe, Scott W.; Stephenson, Corey R. J. [Chemical Communications, 2010, vol. 46, # 27, p. 4985 - 4987]

50
[ 1267475-14-8 ]
[ 69361-41-7 ]
[ 1267475-15-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran for 1.25h; Inert atmosphere; Reflux; Stage #2: With copper(l) iodide; dimethylsulfide In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #3: C₂₉H₃₇NO₄Si In tetrahydrofuran at -40 - -20℃; for 4.66667h; Inert atmosphere;	(R)-3-((R)-3-(3-((E)-3-((tert-butyldimethylsilyl)oxy)prop-1-en-1-yl)phenyl)-7-(trimethylsilyl)hept-6-ynoyl)- 5,5-dimethyl-4-phenyloxazolidin-2-one (11). Grignard reagent 10 was prepared by addition of 4-bromo-1- trimethylsilyl-1-butyne8 (16.4 g, 80 mmol) in THF (80 mL) to magnesium filings (2.92 g, 120 mmol); initial addition of 8 mL followed by dropwise addition of the remainder via syringe pump over 1 h. The solution was warmed to reflux for 15 min, cooled to room temperature, diluted with 80 mL THF and titrated against a standard solution of menthol in THF containing 1,10-phenanthrolein as an indicator (c = 0.50 M). Copper(I) Iodide (10.11 g, 53.1 mmol) was dissolved in THF (90 mL) and dimethylsulfide (22 mL), cooled to -78 °C and stirred for 15 min. The Grignard reagent (101 mL) was added via cannula over 10 minutes, and the mixture was stirred for 10 minutes at -78 oC, then 10 minutes at -40 °C. A pre-cooled solution of 9 (22.53g, 45.8 mmol) in THF (60 mL) was added over 10 minutes, and stirring continued at -40 °C for 30 min and then at -20 °C for 4h. The reaction was quenched with saturated NH4Cl (25 mL) and diluted with H2O (150 mL). The aqueous phase was extracted with EtOAc, and the combined organic phase was washed with H2O, brine, dried over MgSO4, and concentrated. The residue was freed from copper salts by repeated trituration with 1:1 hexane:EtOAc and filtration through short plugs of silica gel. Compound 11 (27.30 g, 96%, single diastereoisomer by 1H NMR) was used without purification. 1H NMR (CDCl3, 400 MHz): d 7.28-7.38 (m, 3H), 7.18-7.24 (m, 3H), 7.05-7.10 (m, 3H), 6.55 (dt, J = 15.8, 1.7 Hz, 1H), 6.27 (dt, J = 15.8, 5.0 Hz, 1H), 4.87 (s, 1H), 4.35 (dd, J = 5.0, 1.7 Hz, 2H), 3.67 (dd, J = 16.2, 9.6 Hz, 1H), 3.27 (dddd, J = 10.0, 9.6, 5.4, 4.9 Hz, 1H), 3.09 (dd, J = 16.2, 5.4 Hz, 1H), 1.75-2.12 (m, 4H), 1.34 (s, 3H), 0.95 (s, 9H), 0.90 (s, 3H), 0.12 (brs, 15H). 13C NMR (CDCl3, 100 MHz): d 171.5, 153.4, 143.1, 137.4, 136.4, 129.5, 129.4, 129.0, 128.8, 128.7, 126.9, 126.1, 124.9, 106.7, 85.1, 82.5, 67.1, 64.0, 41.5, 41.2, 35.4, 28.7, 26.1, 25.8, 23.7, 18.6, 18.1, 0.3, -5.0. HRMS (ESI) Calculated for C36H51NO4Si2 [M+Na]+: 640.3249, found 640.3243.

Reference： [1]Lawson, Kenneth V.; Rose, Tristan E.; Harran, Patrick G. [Tetrahedron Letters, 2011, vol. 52, # 6, p. 653 - 654]

51
[ 18448-47-0 ]
[ 69361-41-7 ]
[ 1332745-33-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Reflux; Inert atmosphere; Stage #2: methyl cyclohex-1-ene-1-carboxylate With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -40℃; for 8h; Inert atmosphere;

Reference： [1]Shi, Hang; Fang, Lichao; Tan, Ceheng; Shi, Lili; Zhang, Weibin; Li, Chuang-Chuang; Luo, Tuoping; Yang, Zhen [Journal of the American Chemical Society, 2011, vol. 133, # 38, p. 14944 - 14947]

52
[ 56745-53-0 ]
[ 69361-41-7 ]
[ 1332745-36-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Reflux; Inert atmosphere; Stage #2: methyl cyclohept-1-ene-1-carboxylate With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -40 - -35℃; for 5h; Inert atmosphere;

Reference： [1]Shi, Hang; Fang, Lichao; Tan, Ceheng; Shi, Lili; Zhang, Weibin; Li, Chuang-Chuang; Luo, Tuoping; Yang, Zhen [Journal of the American Chemical Society, 2011, vol. 133, # 38, p. 14944 - 14947]

53
[ 25662-28-6 ]
[ 69361-41-7 ]
[ 1332745-43-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Reflux; Inert atmosphere; Stage #2: 1-(carboxymethoxy)cyclopentadiene With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -40℃; for 8h; Inert atmosphere;

Reference： [1]Shi, Hang; Fang, Lichao; Tan, Ceheng; Shi, Lili; Zhang, Weibin; Li, Chuang-Chuang; Luo, Tuoping; Yang, Zhen [Journal of the American Chemical Society, 2011, vol. 133, # 38, p. 14944 - 14947]

54
[ 69361-41-7 ]
[ 118653-39-7 ]
[ 1332745-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Reflux; Inert atmosphere; Stage #2: methyl 3,3-dimethyl-6-oxocyclohex-1-ene-1-carboxylate With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl 3,3-dimethyl-6-oxocyclohex-1-ene-1-carboxylate With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	1 A mixture containing magnesium turnings (0.49 g, 20 mmol) and a small piece of iodine in THF (3 mL) was heated to boiling. Grignard reagent having the following structure was prepared by adding dropwise (4-bromo-but-1-ynyl)trimethylsilane in THF solution (10 mL) to the mixture and continued to stir at room temperature for 0.5 hr to prepare the Grignard reagent with following structure: The prepared Grignard reagent was added to a mixture of CuBr·Me2S (0.32 g, 1.56 mmol) in THF solution (40 mL) at -78° C. Then, a mixture of Compound H (0.95 g, 5.2 mmol) in THF solution (27 mL) was added dropwise. After stirring for two hours, saturated NH4Cl aqueous solution (50 mL) was added to quench the reaction. The aqueous phase was extracted with EtOAc (40 mL×2), the organic phases were combined and dried, concentrated by rotary evaporation, and purified by column chromatography (EtOAc/hexane=1/100) to yield yellow oily liquid Compound G.

Reference： [1]Shi, Hang; Fang, Lichao; Tan, Ceheng; Shi, Lili; Zhang, Weibin; Li, Chuang-Chuang; Luo, Tuoping; Yang, Zhen [Journal of the American Chemical Society, 2011, vol. 133, # 38, p. 14944 - 14947]
[2]Current Patent Assignee: TZENG; JENISA BIOTECHNOLOGY; SINGAPORE GREEN CHEMICAL ENGINEERING; YANG - US2014/350096, 2014, A1 Location in patent: Paragraph 0045; 0046; 0047

55
[ 75-77-4 ]
[ 1374425-28-1 ]
[ 69361-41-7 ]
[ 1374425-29-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #3: chloro-trimethyl-silane; C₂₅H₃₀O₃ In tetrahydrofuran at -78℃; for 5h; Inert atmosphere;

Reference： [1]Richard, Jean-Alexandre; Chen, David Y.-K. [European Journal of Organic Chemistry, 2012, # 3, p. 484 - 487]

56
[ 69361-41-7 ]
[ 243853-48-7 ]
[ 1392190-34-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With iodine; magnesium In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere; Stage #2: 1,3,5,7,9-pentachlorocorannulene With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at 0 - 20℃; for 2.5h; Inert atmosphere;
	With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 2.5h;

Reference： [1]Mattarella, Martin; Siegel, Jay S. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5799 - 5802]
[2]Mattarella, Martin; Garcia-Hartjes, Jaime; Wennekes, Tom; Zuilhof, Han; Siegel, Jay S. [Organic and Biomolecular Chemistry, 2013, vol. 11, # 26, p. 4333 - 4339]

57
[ 69361-41-7 ]
[ 460710-34-3 ]
(2S,6R,7S,8S,1'R)-(1"Z)-2-(5'-trimethylsilyl-1'-hydroxypent-4'-ynyl)-7-(4''-trimethylsilyl-but-1''-en-3''-yn-1''-yl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane [ No CAS ]
(2S,6R,7S,8S,1'S)-(1"Z)-2-(5'-trimethylsilyl-1'-hydroxypent-4'-ynyl)-7-(4''-trimethylsilyl-but-1''-en-3''-yn-1''-yl)-1-aza-12-oxatricyclo[5.4.1^6,8.0]undecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 33%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; ethylene dibromide In tetrahydrofuran at 40℃; Inert atmosphere; Stage #2: (2S,6R,7S,8S)-(1'Z)-2-formyl-7-(4'-trimethylsilyl-but-1'-en-3'-yn-1'-yl)-1-aza-12-oxa tricyclo[5.4.1^6,8.0]undecane In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere;

Reference： [1]Hodges, Alastair J.; Bond, Andrew D.; Holmes, Andrew B.; Roughley, Stephen D.; Smith, Catherine J.; Adams, Joseph P.; Ryan, John H.; Saubern, Simon; Newton, Annabella F.; Press, Neil J.; Turnbull, Michael D. [Organic and biomolecular chemistry, 2012, vol. 10, # 45, p. 8963 - 8974,12] Hodges, Alastair J.; Adams, Joseph P.; Bond, Andrew D.; Holmes, Andrew B.; Press, Neil J.; Roughley, Stephen D.; Ryan, John H.; Saubern, Simon; Smith, Catherine J.; Turnbull, Michael D.; Newton, Annabella F. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 45, p. 8963 - 8974]

58
[ 1218815-84-9 ]
[ 69361-41-7 ]
[ 1415391-83-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With magnesium; ethylene dibromide In diethyl ether; dichloromethane at -78℃; for 2h; Inert atmosphere;

Reference： [1]Steward, Kimberly M.; Corbett, Michael T.; Goodman, C. Guy; Johnson, Jeffrey S. [Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20197 - 20206]

59
[ 5381-20-4 ]
[ 69361-41-7 ]
[ 1430475-42-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 9083 - 9090

60
[ 1378705-69-1 ]
[ 69361-41-7 ]
[ 1431618-28-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; Stage #2: 2,2-diethoxy-N-methoxy-N-methyl-acetamide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;

Reference： [1]Sibbersen, Christian; Palmfeldt, Johan; Hansen, Jakob; Gregersen, Niels; Jorgensen, Karl Anker; Johannsen, Mogens [Chemical Communications, 2013, vol. 49, # 38, p. 4012 - 4014]

61
5-isobutyl-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]
[ 69361-41-7 ]
5-isobutyl-1,3-dimethyl-5-(4-(trimethylsilyl)but-3-yn-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With potassium carbonate In acetone at 60℃; for 21h;

Reference： [1]Szostak, Michal; Sautier, Brice; Spain, Malcolm; Behlendorf, Maike; Procter, David J. [Angewandte Chemie - International Edition, 2013, vol. 52, # 48, p. 12559 - 12563][Angew. Chem., 2013, vol. 125, # 48, p. 12791 - 12795,5]

62
[ 133268-26-5 ]
[ 69361-41-7 ]
[ 1607829-52-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran at 20℃; for 3h; Stage #2: With copper(I) bromide dimethylsulfide complex; dimethylsulfide In tetrahydrofuran at -10℃; for 0.333333h; Stage #3: cis-4-Oxa-bicyclo[3.3.0]-7-octen-3-on In tetrahydrofuran at -10℃; for 4h;

Reference： [1]Thaharn, Watcharaporn; Soorukram, Darunee; Kuhakarn, Chutima; Tuchinda, Patoomratana; Reutrakul, Vichai; Pohmakotr, Manat [Angewandte Chemie - International Edition, 2014, vol. 53, # 8, p. 2212 - 2215][Angew. Chem., 2014, vol. 126, # 8, p. 2284]

63
[ 296238-72-7 ]
[ 69361-41-7 ]
benzyl (2-(diethoxyphosphoryl)-1,1,1-trifluoro-6-(trimethylsilyl)hex-5-yn-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium In tetrahydrofuran; ethylene dibromide at 55℃; for 1h; Inert atmosphere; Stage #2: diethyl (N-benzyloxycarbonyl-2,2,2-trifluoroethaneimidoyl)phosphonate In tetrahydrofuran; ethylene dibromide at 20℃; for 0.333333h; Inert atmosphere;	General procedure for the synthesis of starting alkynes 2 General procedure: To a three-necked round-bottom flask, equipped with a thermometer, reflux condenser andmagnetic stirring bar magnesium (0.72g, 30mmol) and 20 ml of freshly distilled THF wereloaded. To the resulting suspension five drops of 1,2-dibromoethane were added in an argonatmosphere and the mixture was stirred for 5 min during which time the temperature slightlyincreased. Then a solution of corresponding alkynylbromide (10 mmol) in dry THF (8 ml) wasadded dropwise during 10 min period, the solution becomes cloudy and the temperatureincreases up to 45°C. Subsequently reaction was maintained at 55°C for 1 hour, then cooled anda solution of the resulted Grignard reagent was carefully transferred to dropping funnel and wasused for the next step.To a stirred solution of CF3-substituted iminophosphonate (6.7 mmol) in dry THF at -78°Cunder an argon atmosphere a solution of Grignard reagent in THF was added dropwise during 20min period. The resulting mixture was slowly warmed to room temperature and was additionallystirred overnight. Then the reaction was quenched by addition of NH4Cl saturated solution inwater (100 ml). The crude product was extracted with EtOAc (3*50ml), combined organicfractions was washed twice with water (100 ml), dried over anhydrous MgSO4. Solvents were evaporated under reduced pressure and remaining viscous oil was fractionated by columnchromatography to afford the desired product.

Reference： [1]Krylov, Ivan M.; Mailyan, Artur K.; Zotova, Maria A.; Bruneau, Christian; Dixneuf, Pierre H.; Osipov, Sergey N. [Synlett, 2014, vol. 25, # 18, p. 2624 - 2628]

64
[ 69361-41-7 ]
C₂₁H₃₅NO₅Si [ No CAS ]
C₂₆H₄₂O₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With magnesium; ethylene dibromide In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Reflux;

Reference： [1]Sokolsky, Alexander; Cattoen, Martin; Smith, Amos B. [Organic Letters, 2015, vol. 17, # 8, p. 1898 - 1901]

65
[ 69361-41-7 ]
C₂₂H₃₆INO₅Si [ No CAS ]
C₂₇H₄₃IO₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 4-bromo-1-trimethylsilylbut-1-yne With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: C₂₂H₃₆INO₅Si In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere;	CompoundS16. To magnesium turnings (660 mg, 27.2 mmol, 5.0 eq) in refluxingTHF (40 mL) was added dibromoethane (230 µL, 2.72 mmol,0.5 eq) and the mixture refluxed an additional 10 minutes. A solution of (4-bromobut-1-yn-1-yl)trimethylsilane6 (3.35 g, 16.3 mmol,3.0 eq, must be free of trace bromoform from the preceeding Appel reaction) inTHF (10 mL) was then added dropwise and the reaction mixture refluxed for anadditional 1h. In a separate flask, a solution of S15 (2.99 g, 5.44 mmol, 1.0 eq) in THF (20 mL) was cooled to -78°C. The Grignard solution was then cooled to room temperature and transferredto the solution of S15 dropwise via syringe and the resulting mixturestirred at -78 °C for 30 min, then at 0 °C for an additional 1.5 h. Thereaction was quenched with sat. aqueous ammonium chloride and diluted withdiethyl ether. The layers were separated and the aqueous layer extracted withadditional diethyl ether. The combined organics were washed with water andbrine, dried over Na2SO4 and concentrated. The residuewas purified by flash column chromatography (9:1 Hexanes:Diethyl ether) toyield the title compound (3.06 g, 92%) as a colorless oil. Rf =0.33in 9:1 Hexanes:Diethyl Ether 1H NMR (CDCl3, 500MHz): δ = 7.26 (d, J = 8.7 Hz, 2 H), 6.92 (d, J = 8.7 Hz, 2 H),6.26 (qd, J = 1.4, 8.0 Hz, 1 H), 4.69 (d, J = 11.8 Hz, 1 H), 4.56(dd, J = 3.9, 7.0 Hz, 1 H), 4.39 (d, J = 11.8 Hz, 1 H), 3.84 (s,3 H), 3.68 (d, J = 3.6 Hz, 1 H), 2.93 - 2.77 (m, 2 H), 2.51 - 2.37 (m, 2H), 2.34 (d, J = 1.5 Hz, 3 H), 0.92 (t, J = 8.1 Hz, 9 H), 0.54(q, J = 8.2 Hz, 6 H), 0.15 (s, 9 H). 13C NMR (CDCl3, 126MHz): δ = 210.3, 159.7, 140.9, 130.1, 129.0, 114.1, 106.1, 96.9, 86.2, 84.9,73.5, 71.7, 55.4, 40.3, 28.5, 13.8, 6.8, 6.8, 6.8, 4.8, 0.2. IR(film): = 2956, 2912, 2877, 2176, 1718, 1637, 1612, 1586, 1514, 1250 cm-1. HRMS (ESI):C27H43O4Si2INa [M+ + Na] 637.1642. Found637.1639. [α]D20 =+56 (c = 0.92 in CH2Cl2)

Reference： [1]Sokolsky, Alexander; Wang, Xiaozhao; Smith, Amos B. [Tetrahedron Letters, 2015, vol. 56, # 23, p. 3160 - 3164]

66
[ 1121-18-2 ]
[ 69361-41-7 ]
C₁₁H₁₆O [ No CAS ]