Name: 61362-77-4|tert-Butyldimethyl(pent-4-yn-1-yloxy)silane|98%
Brand: Ambeed
SKU: A1175600
Rating: 97 (22 reviews)

1
[ 5390-04-5 ]
[ 18162-48-6 ]
[ 61362-77-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 1H-imidazole; In dichloromethane; at 20℃; for 24h;	To a stirred solution of 4-pentyn-l-ol 800 (5 mL, 53.72 mmol) in CH2CI2 ( 150 mL) at r.t. was added imidazole (3.66 g, 53.72 mmol) and terf-butyldimethylsilyl chloride (8.10 g, 53.72 mmol). The reaction mixture was a llowed to stir at r.t. for 24 h. The mixture was then diluted with Et2<D (200 mL) and washed with water (3 x 100 mL) and brine ( 100 mL) . The orga nic layer was dried over anhydrous Na2S04 and concentrated in vacuo. The crude was purified by filtration throug h silica gel to give 801 (10.64 g, quant.) as a colourless liq uid. Alkyne 801 was used in subsequent synthetic steps without characterisation.
99%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	To a magnetically stirred solution of 4-pentynol 8 (5.0 g, 59.4 mmol) and imidazole (10.1 g,148.6 mmol) in dry DMF (100 mL), was added dropwise tert-butyldimethylsilyl chloride (9.4 g, 62.4 mmol) in DMF (50 mL) over 10 min at 0 C under an atmosphere of nitrogen. The reaction mixture was warmed to room temperature and stirred overnight. Water (300 mL) was added and then the reaction mixture was extracted with Et2O (3 x 300 mL), dried (Na2SO4), and evaporated under reduced pressure to leave a light yellow oil. The crude product was purified using silica gel flash chromatography eluting with 5% EtOAc/hexane to give TBS-ether (11.8 g, 147.1, 99%) as acolorless oil.
90%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 12h;	Example; Preparation of 5-(tert-butyldimethylsiloxy)pent-1-yne; 5.00 g (59.4 mmol) of pent-1-yn-5-ol were dissolved in 50 ml of dry DMF, and 10.10 g (149 mmol, 2.5 eq.) of imidazole and 9.40 g (62.4 mmol, 1.1 eq.) of TBS-Cl were added. After 12 hours of stirring at RT, 250 ml of water were added and the mixture was extracted with 3×150 ml of MTBE. The organic phase was washed 3× with in each case 100 ml of water and then dried over MgSO4. Purification by column chromatography gave 11.10 g (53.5 mmol, 90%) of 5-(tert-butyldimethylsiloxy)pent-1-yne as a colorless oil.C9H22O2Si1, MW 190.36 g/mol; TLC (cyclohexane/EA 10:1): Rf=0.38.1H-NMR (300 MHz; CDCl3): δ [ppm]=0.01 (s, 6H, SiMe2); 0.85 (s, 9H, Si-CMe3); 1.88 (t, 4J=3.5 Hz, 1H, H-1); 2.22 (dt, 4J=3.5 Hz, 3J=7 Hz, 2H, H-3); 3.65 (t, 3J=6 Hz, 2H, H-5).13C-NMR (75 MHz; CDCl3): δ [ppm]=-5.8 (q, OSiMe2); 14.8 (t, C-3); 18.3 (s, -OCMe3); 25.9 (q, -OCMe3); 31.5 (t, C-4); 61.4 (t, C-5); 83.1 (s,); 68.2 (d, C-1); 84.2 (s, C-2).

80%	With triethylamine; In dichloromethane; at 0 - 20℃; for 18h;	To a stirred solution of 4-pentyn-1-ol (2.98 g, 35.4 mmol) in CH2Cl2 (45.0 mL) were added TBSCl (6.39 g, 42.6 mmol) and Et3N (5.40 g, 53.2 mmol) at 0 C. After stirred for 18 h at room temperature, the suspension was filtered through a Celite Pad and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: hexane/AcOEt = 98:2) to afford the silyl ether S2 (5.60 g, 80%) as a colorless oil. Rf = 0.55 (hexane/AcOEt = 95:5) 1H NMR spectrum of the ester was identical with that previously reported.18 1H NMR (300 MHz, CDCl3) δ 3.70 (2H, t, J = 6.0 Hz), 2.27 (2H, t, J = 6.0 Hz), 1.93 (1H, s), 1.73-1.68(2H, m), 0.90 (9H, s), 0.057 (6H, s).
58%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20 - 30℃; for 4h;	A solution of 2.2 ml (0.024 moles) of commercial 5-hydroxy-1-pentyne and 4.0 g (0.059 moles) of imidazole and 4.01 g (0.026 moles) of t-butyldimethylsilyl chloride in 4 ml of dimethylformamide is left under stirring at room temperature (20-30 C.) until TLC (3/7 diethyl ether/petroleum ether) reveals disappearance of starting 5-hydroxy-1-pentyne and appearance of a spot with higher Rf. Usually, the disappearance of the starting product is observed after about 4 hours. The reaction mixture is diluted with water, the aqueous phase is extracted with ethyl ether and the combined organic phases are washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. After solvent evaporation and distillation of the crude product under reduced pressure, 2.791 g (0.014 moles) of 5-(t-butyldimethylsilyloxy)pent-1-yne which distils at 67 C. at 23 mbars is obtained. Yield: 58%.1H-NMR (CDCl3): δ 3.71 (t, 2H), 2.29 (td, 2H), 1.93 (t, 1H), 1.74 (q, 2H), 0.90 (s, 9H), 0.05 (s, 6H).
58%	With 1H-imidazole; In N,N-dimethyl-formamide; at 2 - 30℃; for 2 - 4h;Product distribution / selectivity;	A solution of 2.2 ml (0.024 moles) of commercial 5-hydroxy-l-pentyne and 4.0 g (0.059 moles) of imidazole and 4.01 g (0.026 moles) of t-butyldimethylsilyl chloride in 4 ml of dimethyl formamide is left under stirring at room temperature (20-300C) until TLC (3/7 diethyl ether/petroleum ether) reveals disappearance of starting 5-hydroxy-l-pentyne and appearance of a spot with higher R/. Usually, the disappearance of the starting product is observed after about 4 hours. The reaction mixture is diluted with water, the aqueous phase is extracted with ethyl ether and the combined organic phases are washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. After solvent evaporation and distillation of the crude product under reduced pressure, 2.791 g (0.014 moles) of5-(t-butyldimethylsilyloxy)pent-l-yne which distils at 67C at 23 mbars is obtained. Yield: 58%.1H-NMR (CDCl3): δ 3.71 (t, 2H), 2,29 (td, 2H), 1.93 (t, IH), 1.74 (q, 2H), 0.90 (s, 9H), 0.05 (s, 6H).; 5- (t-Butyldimethylsilyloxy)pent- 1 -yne A mixture of 186 ml of dimethylformamide, 93.5 g of 5-hydroxy-l- pentyne and 185.5 g of imidazole at room temperature (20-300C) is added with 185.5 g of t-butyldimethylsilyl chloride, in portions and under stirring, keeping this temperature with cooling bath. The resulting pale-yellow, dense suspension is cooled to 2C, kept under stirring and monitored by TLC (eluent 7/3 diethyl ether /petroleum ether, developer: hot perchloric acid; R/ of the starting product = 0.33, R/ of the final product = 0.95); the reaction is complete after two hours. The reaction mixture is slowly added with 375 ml of water and 150 ml of toluene, and stirring is continued for 10 minutes, EPO <DP n="24"/>controlling the temperature with cooling bath. The organic phase is separated, the aqueous one is extracted with 100 ml of toluene, then combined organic phases are filtered under reduced pressure through Celite, washing the cake with 50 ml of toluene. The solution is concentrated under reduced pressure to obtain a pale-yellow oily residue which is distilled at a temperature ranging from 23 to 340C at about 13 mbars and subsequently at 7.5 mbars at a temperature ranging from 35 to 6O0C. The two resulting fractions are discarded. Continuing the distillation at 7.5 mbars, the fractions which distil above 600C are collected. The first fraction, which distils between 60 and 750C (89 g) is in turn discarded whereas the second one, which distils at 75C, consists of 101 g of 5-(t-butyldimethylsilyloxy)pent-l-yne identical to the product of preparation I.
	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 60h;	To a solution of 48 (1.0 mL, 11 mmol, 1.0 equiv.) in DMF(30 mL) was added tert-butyldimethylchlorosilane (2.1 g, 14 mmol, 1.3 equiv.), then imidazole (1.8 g, 26 mmol, 2.5 equiv.). The mixture was stirred at room temperature (60 h), then filtered. The filtrate was diluted with hexanes (100 mL), washed with water (3100 mL), brine (100 mL), dried over sodium sulfate and passed through a plug of silica, washing withCH2Cl2/hexanes 1 : 9 (50 mL), and concentrated to give acolourless oil. This colourless oil was taken up in methanol(25 mL) and a solution of potassium hydroxide (1.5 g, 27 mmol,2.5 equiv.) in water (7 mL) added. The mixture was cooled to 0C and stirred with protection from light while iodine (4.1 g,16 mmol, 1.5 equiv.) was added in small portions, allowing the brown colour of dissolved iodine to dissipate between portions. The mixture was stirred for a further 16 h, while being allowed to warm to room temperature. The reaction mixture was partitioned between hexanes (100 mL) and water (100 mL). The aqueous partition was washed with hexanes (50 mL) and the hexane wash combined with the organic partition of the reaction mixture, and washed with water (3100 mL), brine (50 mL),dried over NaSO4, and concentrated. Column chromatography(ether/light petroleum 1 : 9) gave 49 (2.6 g, 74 %) as a slightly yellow oil. Rf 0.25 (EtOAc/hexanes 1 : 50). νmax (neat)/cm12190, 1471, 1253, 1007, 835, 776. δH (300 MHz, CDCl3) 3.67(2H, d, J 6.1), 2.44 (2H, t, J 7.0), 1.72 (2H, dt, J 13.9, 6.4), 0.88(9H, s), 0.03 (3H, s). δC (75 MHz, CDCl3) 94.2 (C), 61.3 (CH2),31.4 (C), 25.9 (3C, CH3), 18.3 (CH2), 17.3 (CH2), 5.3 (2C,CH3), 7.1 (CI).
	With 1H-imidazole; In dichloromethane; at 20℃; for 24h;	To a stirred solution of 4-pentyn-l-ol 800 (5 mL, 53.72 mmol) in CH2CI2 (150 mL) at r.t. was added imidazole (3.66 g, 53.72 mmol) and terf-butyldimethylsilyl chloride (8.10 g, 53.72 mmol). The reaction mixture was allowed to stir at r.t. for 24 h. The mixture was then diluted with Et2
	With 1H-imidazole; In N,N-dimethyl-formamide; for 2h;	Example 1. Step 1: /ert-Butyl-dimethyl-pent-4-ynyloxy-silane[00399] 4-Pentyn-1-ol (5g, 59.4mmol) was dissolved in DMF (10OmL). Imidazole (4.2g, 62.3mmol) was added, followed by tert-butyldimethylsilyl chloride (δ.5g, 56.6mmol), and the reaction was stirred for 2 hours. The mixture was diluted with hexanes and H2O, and the organic layer was dried and concentrated to give the title compound.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1469 - 1472
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5062 - 5078
[3]Chemistry - A European Journal,2015,vol. 21,p. 11590 - 11602
[4]Chemistry - A European Journal,2016,vol. 22,p. 8777 - 8780
[5]Patent: WO2019/43604,2019,A1 .Location in patent: Page/Page column 141
[6]Journal of Medicinal Chemistry,2020,vol. 63,p. 2282 - 2291
[7]Angewandte Chemie, International Edition,2020,vol. 59,p. 16625 - 16630
    Angew. Chem.,2020,vol. 132,p. 16768 - 16773,6
[8]Organic Letters,2005,vol. 7,p. 3921 - 3924
[9]Angewandte Chemie - International Edition,2006,vol. 45,p. 4767 - 4771
[10]Journal of the Chinese Chemical Society,2007,vol. 54,p. 525 - 532
[11]Tetrahedron,2008,vol. 64,p. 3464 - 3470
[12]Tetrahedron,2016,vol. 72,p. 2280 - 2286
[13]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3556 - 3559
[14]Chemistry - A European Journal,2021,vol. 27,p. 14846 - 14850
[15]Journal of Organic Chemistry,1998,vol. 63,p. 4291 - 4298
[16]Organic Letters,2018,vol. 20,p. 119 - 121
[17]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1875 - 1878
[18]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 2243 - 2250
[19]Journal of Organic Chemistry,2002,vol. 67,p. 7774 - 7780
[20]Journal of the American Chemical Society,2012,vol. 134,p. 16080 - 16084
[21]Journal of the American Chemical Society,1989,vol. 111,p. 5330 - 5334
[22]Canadian Journal of Chemistry,1992,vol. 70,p. 2058 - 2064
[23]Organic letters,2002,vol. 4,p. 885 - 888
[24]Organic Letters,2002,vol. 4,p. 3443 - 3446
[25]Organic Letters,2011,vol. 13,p. 998 - 1000
[26]Journal of the American Chemical Society,2011,vol. 133,p. 18194 - 18201
[27]Organic Letters,2019,vol. 21,p. 10048 - 10051
[28]Journal of the American Chemical Society,1994,vol. 116,p. 549 - 557
[29]Tetrahedron Letters,1997,vol. 38,p. 7379 - 7382
[30]Organic Letters,2015,vol. 17,p. 3868 - 3871
[31]Journal of the American Chemical Society,1991,vol. 113,p. 6621 - 6633
[32]Journal of the American Chemical Society,2009,vol. 131,p. 9178 - 9179
[33]Journal of the American Chemical Society,2010,vol. 132,p. 1895 - 1902
[34]Organic Letters,2011,vol. 13,p. 1781 - 1783
[35]Organic Letters,2015,vol. 17,p. 1754 - 1757
[36]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9012 - 9020
[37]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4842 - 4850
[38]Journal of Organic Chemistry,1986,vol. 51,p. 863 - 872
[39]Journal of Organic Chemistry,2005,vol. 70,p. 8281 - 8290
[40]Organic Letters,2002,vol. 4,p. 1651 - 1654
[41]Tetrahedron Letters,2009,vol. 50,p. 4164 - 4166
[42]Journal of the American Chemical Society,2003,vol. 125,p. 15878 - 15892
[43]Patent: US2009/156836,2009,A1 .Location in patent: Page/Page column 12
[44]Angewandte Chemie - International Edition,2014,vol. 53,p. 14051 - 14054
    Angew. Chem.,2014,p. 14275 - 14278,4
[45]Organic Letters,2019,vol. 21,p. 9934 - 9939
[46]Synthesis,2003,p. 2699 - 2704
[47]Organic Letters,2019,vol. 21,p. 6628 - 6632
[48]Journal of Chemical Research, Miniprint,1998,p. 614 - 634
[49]Tetrahedron,2009,vol. 65,p. 3270 - 3280
[50]Journal of Medicinal Chemistry,2020,vol. 63,p. 15960 - 15978
[51]Organic Letters,2011,vol. 13,p. 3178 - 3181
[52]Organic Letters,2015,vol. 17,p. 5517 - 5519
[53]Heterocycles,2019,vol. 99,p. 875 - 890
[54]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1542 - 1550
[55]Chemistry - A European Journal,2013,vol. 19,p. 7125 - 7132
[56]Journal of Organic Chemistry,2013,vol. 78,p. 12735 - 12749
[57]Bulletin de la Societe Chimique de France,1997,vol. 134,p. 349 - 356
[58]Journal of the American Chemical Society,2014,vol. 136,p. 16140 - 16143
[59]Chemistry and biodiversity,2009,vol. 6,p. 1 - 37
[60]Heterocycles,2001,vol. 54,p. 1049 - 1055
[61]Angewandte Chemie - International Edition,2020,vol. 59,p. 6750 - 6755
    Angew. Chem.,2020,vol. 132,p. 6816 - 6821,6
[62]Bulletin of the Chemical Society of Japan,2010,vol. 83,p. 619 - 634
[63]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 989 - 995
[64]Patent: US2010/35796,2010,A1 .Location in patent: Page/Page column 8
[65]Patent: WO2007/14711,2007,A1 .Location in patent: Page/Page column 22; 23
[66]Organic Letters,2016,vol. 18,p. 2608 - 2611
[67]Synthetic Communications,1976,vol. 6,p. 503 - 508
[68]Synthesis,1997,p. 1315 - 1320
[69]Tetrahedron Letters,1998,vol. 39,p. 2861 - 2864
[70]Synlett,2006,p. 419 - 422
[71]Journal of the American Chemical Society,2000,vol. 122,p. 4990 - 4991
[72]Organic Letters,2001,vol. 3,p. 1049 - 1052
[73]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 635 - 637
[74]Chemistry - A European Journal,2012,vol. 18,p. 14618 - 14621
[75]Journal of the American Chemical Society,2014,vol. 136,p. 6255 - 6258
[76]Australian Journal of Chemistry,2015,vol. 68,p. 555 - 565
[77]Organic Letters,2015,vol. 17,p. 2098 - 2101
[78]Chemistry - A European Journal,2015,vol. 21,p. 12627 - 12639
[79]Patent: WO2017/145097,2017,A2 .Location in patent: Page/Page column 139; 140
[80]Patent: WO2009/140642,2009,A2 .Location in patent: Page/Page column 84
[81]Organic Letters,2020,vol. 22,p. 755 - 759
[82]Organic Letters,2021,vol. 23,p. 3190 - 3194
[83]Journal of Medicinal Chemistry,2021,vol. 64,p. 17287 - 17303
[84]Journal of the American Chemical Society,2022,vol. 144,p. 4770 - 4775

2
[ 50-00-0 ]
[ 61362-77-4 ]
[ 100571-18-4 ]

Reference： [1]Journal of the Chinese Chemical Society,2007,vol. 54,p. 525 - 532
[2]Tetrahedron Letters,2009,vol. 50,p. 4164 - 4166
[3]Chemistry - A European Journal,2015,vol. 21,p. 11590 - 11602
[4]Journal of Organic Chemistry,2002,vol. 67,p. 7774 - 7780
[5]Journal of Organic Chemistry,2009,vol. 74,p. 2907 - 2910
[6]Organic Letters,2019,vol. 21,p. 10048 - 10051
[7]Journal of the American Chemical Society,2011,vol. 133,p. 18194 - 18201
[8]Journal of the American Chemical Society,2009,vol. 131,p. 9178 - 9179
[9]Heterocycles,2001,vol. 54,p. 1049 - 1055
[10]Journal of Organic Chemistry,2005,vol. 70,p. 8281 - 8290
[11]Organic Letters,2002,vol. 4,p. 1651 - 1654
[12]Journal of the American Chemical Society,2014,vol. 136,p. 13932 - 13939
[13]Journal of the American Chemical Society,1989,vol. 111,p. 5330 - 5334
[14]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3556 - 3559
[15]Chemistry - A European Journal,2021,vol. 27,p. 14846 - 14850
[16]Journal of the American Chemical Society,1991,vol. 113,p. 6621 - 6633
[17]Journal of Organic Chemistry,1986,vol. 51,p. 863 - 872
[18]Journal of the Chemical Society. Chemical communications,1985,p. 1359 - 1362
[19]Tetrahedron,1997,vol. 53,p. 13797 - 13810
[20]Journal of Organic Chemistry,1998,vol. 63,p. 5962 - 5970
[21]Journal of Organic Chemistry,2004,vol. 69,p. 2128 - 2136
[22]Angewandte Chemie - International Edition,2015,vol. 54,p. 6582 - 6586
Angew. Chem.,2015,vol. 127,p. 6682 - 6686,5
[23]Organic Letters,2016,vol. 18,p. 676 - 679
[24]Journal of the American Chemical Society,2022,vol. 144,p. 4770 - 4775

3
[ 61362-77-4 ]
[ 112373-73-6 ]
tert-Butyl-dimethyl-[(E)-7-((R)-toluene-4-sulfinyl)-hept-6-en-4-ynyloxy]-silane [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3663 - 3666
[2]Journal of Organic Chemistry,1997,vol. 62,p. 6326 - 6343

4
[ 61362-77-4 ]
[ 541-41-3 ]
[ 101849-55-2 ]

Reference： [1]Synlett,2010,p. 2617 - 2620
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4842 - 4850
[3]Journal of Organic Chemistry,1990,vol. 55,p. 2374 - 2379
[4]Organic Letters,2001,vol. 3,p. 1049 - 1052

5
[ 61362-77-4 ]
[ 123-38-6 ]
[ 154491-81-3 ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 1413 - 1421
[2]Journal of the American Chemical Society,1994,vol. 116,p. 549 - 557

6
[ 61362-77-4 ]
[ 79-22-1 ]
[ 145383-97-7 ]

Yield	Reaction Conditions	Operation in experiment
87%		To a solution of S2 (890 mg, 4.48 mmol) in THF (17.2 mL) was added BuLi (1.6 M in hexane, 3.6 mL, 5.82 mmol) at -78 C. After stirred for 20 min, methyl chloroformate (550 mg, 5.82 mmol) was added to the reaction mixture at the same temperature. After stirred for 3 h at 0 C, the reaction was quenched with sat. aqueous NH4Cl and aqueous phase was extracted with Et2O. The combined organic phases were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: hexane/AcOEt = 98:2) to afford the ester 27 (1.00 g, 87%) as a colorless oil. Rf = 0.39 (hexane/AcOEt = 95:5) 1H NMR spectrum of the ester was identical with that previously reported.19 1H NMR (300 MHz, CDCl3) δ 3.75 (3H, s), 3.68 (2H, t, J = 6.0 Hz), 2.43 (2H, t, J = 6.9 Hz), 1.77 (2H, tt,J = 6.9, 6.0 Hz), 0.88 (9H, s), 0.046 (6H, s).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1469 - 1472
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5062 - 5078
[3]Heterocycles,2019,vol. 99,p. 875 - 890
[4]Journal of the American Chemical Society,2010,vol. 132,p. 1895 - 1902
[5]Canadian Journal of Chemistry,1992,vol. 70,p. 2058 - 2064
[6]Organic Letters,2015,vol. 17,p. 5517 - 5519

7
[ 61362-77-4 ]
[ 79-44-7 ]
[ 104803-35-2 ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 6265 - 6268
[2]Canadian Journal of Chemistry,1994,vol. 72,p. 2468 - 2482

8
[ 61362-77-4 ]
[ 121-46-0 ]
dimethyl(1,1-dimethylethyl)<(3-(tetracyclo<4.3.0.0^2,4.0^3,7>non-8-enyl)-1-propyl)oxy>silane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 6863 - 6879

9
[ 61362-77-4 ]
[ 104066-69-5 ]

Reference： [1]Bulletin de la Societe Chimique de France,1997,vol. 134,p. 349 - 356
[2]Chemistry Letters,1997,p. 27 - 28
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 6750 - 6755
Angew. Chem.,2020,vol. 132,p. 6816 - 6821,6

10
[ 61362-77-4 ]
[ 18162-48-6 ]
[ 200886-05-1 ]

Reference： [1]Synlett,1999,p. 705 - 708
[2]Synthesis,1997,p. 1315 - 1320

11
[ 104-53-0 ]
[ 61362-77-4 ]
[ 207409-21-0 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 8097 - 8100
[2]Journal of the American Chemical Society,2010,vol. 132,p. 1895 - 1902
[3]Journal of Chemical Research, Miniprint,1998,p. 614 - 634
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 9398 - 9402

12
[ 61362-77-4 ]
[ 100-52-7 ]
[ 207409-19-6 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of alkyne (6 mmol) in THF (6 mL) at -78 C was added dropwisen-BuLi (1.6 M in hexane, 3.1 mL, 5 mmol). After stirring for 30 min, aldehyde (5mmol) was added and the solution warmed to 0 C. After 6 h, the solution wasquenched with sat. aq. NH4Cl, the mixture was extracted with Et2O, dried over Na2SO4,filtered, and concentrated under reduced pressure. The crude product was purified bycolumn chromatography (SiO2, eluted with hexane/EtOAc) to afford the desiredpropargylic alcohol 1.

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 614 - 634
[2]Organic Letters,2012,vol. 14,p. 2586 - 2589
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 9398 - 9402
[4]Synlett,2014,vol. 25,p. 1178 - 1180
[5]Organic Letters,2016,vol. 18,p. 676 - 679

13
[ 61362-77-4 ]
[ 2043-61-0 ]
[ 207409-22-1 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 6366 - 6371
[2]Journal of Chemical Research, Miniprint,1998,p. 614 - 634

14
[ 61362-77-4 ]
[ 33513-42-7 ]
[ 100571-19-5 ]

Reference： [1]Synlett,2010,p. 2617 - 2620
[2]Tetrahedron Letters,1998,vol. 39,p. 6427 - 6428
[3]Chemical Communications,2003,p. 2550 - 2551
[4]Tetrahedron Letters,2007,vol. 48,p. 7906 - 7910
[5]Chemistry - A European Journal,2012,vol. 18,p. 14618 - 14621
[6]ARKIVOC,2012,vol. 2012,p. 253 - 273
[7]Journal of Medicinal Chemistry,2021,vol. 64,p. 17287 - 17303

15
[ 61362-77-4 ]
[ 154698-93-8 ]
[ 193292-63-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 6433 - 6454

16
[ 76-09-5 ]
[ 61362-77-4 ]
(Z)-tert-butyldimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)oxy)silane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 4990 - 4991

17
[ 61362-77-4 ]
[ 75-24-1 ]
[ 100-44-7 ]
[ 345895-27-4 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 3842 - 3843

18
[ 61362-77-4 ]
[ 98-88-4 ]
(E)-6-(tert-butyldimethylsilyloxy)-1-phenylhex-2-en-1-one [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2006,vol. 691,p. 1462 - 1465

19
[ 61362-77-4 ]
[ 107-11-9 ]
(E)-5-[4-(tert-butyldimethylsiloxy)butyl]-4-[4-(tert-butyldimethylsiloxy)butylidene]-3-methyl-3,4-dihydro-2H-pyrrole [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4641 - 4643

20
[ 76-09-5 ]
[ 61362-77-4 ]
[ 277331-67-6 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 4767 - 4771

21
[ 3268-49-3 ]
[ 61362-77-4 ]
(E)-8-(tert-butyl-dimethyl-silyloxy)-1-(methylsulfanyl)-oct-4-en-3-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5291 - 5297

22
[ 61362-77-4 ]
[ 386742-95-6 ]
[ 386742-86-5 ]

Reference： [1]Chemical Communications,2001,p. 2030 - 2031

23
[ 61362-77-4 ]
[ 128084-44-6 ]
[ 944708-24-1 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 2581 - 2584

24
[ 61362-77-4 ]
[ 121353-83-1 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 8281 - 8290
[2]Journal of Organic Chemistry,2002,vol. 67,p. 7774 - 7780
[3]Organic Letters,2002,vol. 4,p. 1651 - 1654
[4]Journal of the American Chemical Society,1989,vol. 111,p. 5330 - 5334
[5]Journal of the American Chemical Society,1991,vol. 113,p. 6621 - 6633
[6]Journal of the American Chemical Society,2014,vol. 136,p. 13932 - 13939
[7]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3556 - 3559

25
[ 61362-77-4 ]
[ 80106-30-5 ]