Name: 23277-00-1|(Naphthalen-1-ylmethyl)triphenylphosphonium chloride|95%
Brand: Ambeed
SKU: A147255
Price: 13.0 USD
Availability: InStock
Rating: 90 (40 reviews)

1
[ 603-35-0 ]
[ 86-52-2 ]
[ 23277-00-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	In toluene;Reflux;	<strong>[86-52-2]1-Chloromethylnaphthalene</strong> (5 g, 28.30 mmol) and triphenylphosphine (7.42 g, 28.30 mmol) weresuspended in 50 mL toluene and the solution was refluxed overnight. During reaction, a whiteprecipitate formed. It was filtered off, washed several times with ether and dried under vacuum(12.15 g, 98% yield).

Reference： [1]Molecules,2017,vol. 22
[2]Tetrahedron,1994,vol. 50,p. 4691 - 4698
[3]Journal of Medicinal Chemistry,1988,vol. 31,p. 807 - 814
[4]Organic Letters,2017,vol. 19,p. 2042 - 2045
[5]Archiv der Pharmazie,1990,vol. 323,p. 253 - 254
[6]Journal of Organic Chemistry USSR (English Translation),1985,vol. 21,p. 354 - 359
Zhurnal Organicheskoi Khimii,1985,vol. 21,p. 392 - 398
[7]Chemische Berichte,1961,vol. 94,p. 2002 - 2010
[8]Chemische Berichte,1961,vol. 94,p. 446 - 450
[9]Bulletin of the Chemical Society of Japan,1972,vol. 45,p. 3638 - 3645
[10]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 679 - 683
[11]Journal of Organic Chemistry,1994,vol. 59,p. 7395 - 7400
[12]Helvetica Chimica Acta,2011,vol. 94,p. 1359 - 1388

2
[ 50-00-0 ]
[ 23277-00-1 ]
[ 826-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate In ethanol

Reference： [1]Zander,M.; Franke,W. [Chemische Berichte, 1961, vol. 94, p. 446 - 450]

3
[ 51359-78-5 ]
[ 23277-00-1 ]
[ 101937-30-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium ethoxide In ethanol

Reference： [1]Drefahl,G. et al. [Chemische Berichte, 1961, vol. 94, p. 2002 - 2010]

4
3-[1]naphthyl-acrylaldehyde [ No CAS ]
[ 23277-00-1 ]
[ 16620-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	With phenyllithium

Reference： [1]Yasuhara,A. et al. [Bulletin of the Chemical Society of Japan, 1972, vol. 45, p. 3638 - 3645]

5
[ 23277-00-1 ]
[ 6630-33-7 ]
[ 76670-39-8 ]

Yield	Reaction Conditions	Operation in experiment
77%
	(i) KOtBu, (ii) /BRN= 636132/; Multistep reaction;
	With tetra(n-butyl)ammonium hydroxide In dichloromethane at 20℃;	Wittig-Mallory Sequential Phenacene Synthesis; Typical Procedure General procedure: To a solution of (1-naphthylmethyl)triphenylphosphonium chloride (55 mg, 125 μmol) and o-tolualdehyde (16 mg, 130 μmol) in CH2Cl2 (10 mL) was added dropwise a solution of Bu4NOH (34 mM in CH2Cl2, 5 mL, 175 μmol) over 12 min. The solution was diluted with CH2Cl2 (5mL) and stirred at r.t. for 18 min. The resulting Wittig reaction mixture was introduced into the flow reaction apparatus (Figure 2). The excess Bu4NOH, H2O, and a part of triphenylphosphine oxide in the reaction mixture were trapped with a silica gel column. The solution that flowed out from the column was mixed with the same volume of solution of I2 (16 mg, 64 μmol) in toluene (100 mL) through a ‘T’-shaped connector and irradiated with a 450 W high-pressure mercury arc lamp. The residence time in the photoreaction coil was set to 6 min (cf. Figure 2). The finally obtained reaction solution was concentrated under reduced pressure and the residual crude product was washed with MeOH to afford 1MeCH (24 mg, 78 %). In the above protocol, the products were isolated after washing the crude reaction mixture with MeOH. In some cases, the final products were isolated by column chromatography (Table 1, entries 9 and 18) or recrystallization (Table 1, entry 17).

Reference： [1]Archer, William J.; Taylor, Roger; Gore, Peter H.; Kamounah, Fadhil S. [Journal of the Chemical Society. Perkin transactions II, 1980, # 12, p. 1828 - 1831]
[2]Gore,P.H.; Kamonah,F.S. [Synthesis, 1978, p. 773 - 775]
[3]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

6
[ 3132-99-8 ]
[ 23277-00-1 ]
[ 76670-40-1 ]

Yield	Reaction Conditions	Operation in experiment
37%
	With tetra(n-butyl)ammonium hydroxide In dichloromethane at 20℃;	Wittig-Mallory Sequential Phenacene Synthesis; Typical Procedure General procedure: To a solution of (1-naphthylmethyl)triphenylphosphonium chloride (55 mg, 125 μmol) and o-tolualdehyde (16 mg, 130 μmol) in CH2Cl2(10 mL) was added dropwise a solution of Bu4NOH (34 mM in CH2Cl2, 5 mL, 175 μmol) over 12 min. The solution was diluted with CH2Cl2 (5mL) and stirred at r.t. for 18 min. The resulting Wittig reaction mixture was introduced into the flow reaction apparatus (Figure 2). The excess Bu4NOH, H2O, and a part of triphenylphosphine oxide in the reaction mixture were trapped with a silica gel column. The solution that flowed out from the column was mixed with the same volume of solution of I2 (16 mg, 64 μmol) in toluene (100 mL) through a ‘T’-shaped connector and irradiated with a 450 W high-pressure mercury arc lamp. The residence time in the photoreaction coil was set to 6 min (cf. Figure 2). The finally obtained reaction solution was concentrated under reduced pressure and the residual crude product was washed with MeOH to afford 1MeCH (24 mg, 78 %). In the above protocol, the products were isolated after washing the crude reaction mixture with MeOH. In some cases, the final products were isolated by column chromatography (Table 1, entries 9 and 18) or recrystallization (Table 1, entry 17).

Reference： [1]Archer, William J.; Taylor, Roger; Gore, Peter H.; Kamounah, Fadhil S. [Journal of the Chemical Society. Perkin transactions II, 1980, # 12, p. 1828 - 1831]
[2]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

7
[ 502-70-5 ]
[ 23277-00-1 ]
[ 38607-87-3 ]
[ 112549-28-7 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) Et₂O, 1 h, r. t., 2) CH₂Cl₂, 2 h, r. t.; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Effenberger, Franz; Schlosser, Hubert; Baeuerle, Peter; Maier, Stefan; Port, Helmut; Wolf, Hans Christoph [Angewandte Chemie, 1988, vol. 100, # 2, p. 274 - 277]

8
[ 3034-50-2 ]
[ 23277-00-1 ]
[ 75840-94-7 ]
[ 75840-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium In ethanol for 3h; Heating;

Reference： [1]Lindberg, Gerd; Stensioe, Karl-Erland; Wahlberg, Kerstin [Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 679 - 683]

9
[ 5056-17-7 ]
[ 23277-00-1 ]
[ 112549-19-6 ]
[ 112549-22-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) Et₂O, 1 h, r. t., 2) CH₂Cl₂, 1 h, r. t.; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Effenberger, Franz; Schlosser, Hubert; Baeuerle, Peter; Maier, Stefan; Port, Helmut; Wolf, Hans Christoph [Angewandte Chemie, 1988, vol. 100, # 2, p. 274 - 277]

10
[ 23277-00-1 ]
[ 112549-18-5 ]
[ 112549-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) Et₂O, 1 h, r. t., 2) CH₂Cl₂, 2 h, r. t.; Yield given. Multistep reaction;

Reference： [1]Effenberger, Franz; Schlosser, Hubert; Baeuerle, Peter; Maier, Stefan; Port, Helmut; Wolf, Hans Christoph [Angewandte Chemie, 1988, vol. 100, # 2, p. 274 - 277]

11
[ 23277-00-1 ]
[ 112549-27-6 ]
[ 112549-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) Et₂O, 1 h, r. t. 2) CH₂Cl₂, 15 h, r. t.; Yield given. Multistep reaction;

Reference： [1]Effenberger, Franz; Schlosser, Hubert; Baeuerle, Peter; Maier, Stefan; Port, Helmut; Wolf, Hans Christoph [Angewandte Chemie, 1988, vol. 100, # 2, p. 274 - 277]

12
[ 23277-00-1 ]
[ 112549-32-3 ]
[ 112549-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) Et₂O, 1 h, r. t., 2) CH₂Cl₂, 2 h, r. t.; Yield given. Multistep reaction;

Reference： [1]Effenberger, Franz; Schlosser, Hubert; Baeuerle, Peter; Maier, Stefan; Port, Helmut; Wolf, Hans Christoph [Angewandte Chemie, 1988, vol. 100, # 2, p. 274 - 277]

13
[ 23277-00-1 ]
[ 112549-31-2 ]
[ 112549-35-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) Et₂O, 1 h, r. t., 2) CH₂Cl₂, 3 h, r. t.; Yield given. Multistep reaction;

Reference： [1]Effenberger, Franz; Schlosser, Hubert; Baeuerle, Peter; Maier, Stefan; Port, Helmut; Wolf, Hans Christoph [Angewandte Chemie, 1988, vol. 100, # 2, p. 274 - 277]

14
[ 23277-00-1 ]
[ 141863-12-9 ]
ethyl <3-(1-naphthyl)-2-tert-butylthiomethyl>-acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) THF, 20 deg C, 4 h; 2.) THF, 35 deg C, 2 h; Yield given. Multistep reaction;

Reference： [1]Beck; Jendralla; Kammermeier [Tetrahedron, 1994, vol. 50, # 16, p. 4691 - 4698]

15
[ 23277-00-1 ]
[ 90-12-0 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide In ethanol; water Heating;

Reference： [1]Listvan, V. N.; Stasyuk, A. P. [Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 2, p. 354 - 359][Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 2, p. 392 - 398]

16
[ 23277-00-1 ]
[ 50675-21-3 ]
1-methyl-4-(1-naphthylvinyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In methanol; diethyl ether for 72h; Ambient temperature;

Reference： [1]Gray, Allan P.; Platz, Robert D.; Henderson, Theresa R.; Chang, Timothy C. P.; Takahashi, Kazuyuki; Dretchen, Kenneth L. [Journal of Medicinal Chemistry, 1988, vol. 31, # 4, p. 807 - 814]

17
[ 23277-00-1 ]
[ 1122-91-4 ]
1-(4-bromophenyl)-2-(1-naphthyl)ethylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%
	Stage #1: 1-naphthylmethyltriphenylphosphonium chloride With lithium hydroxide monohydrate In isopropyl alcohol for 0.333333h; Stage #2: 4-bromo-benzaldehyde In isopropyl alcohol for 16h; Reflux;
	With tetra(n-butyl)ammonium hydroxide In dichloromethane at 20℃;	Wittig-Mallory Sequential Phenacene Synthesis; Typical Procedure General procedure: To a solution of (1-naphthylmethyl)triphenylphosphonium chloride (55 mg, 125 μmol) and o-tolualdehyde (16 mg, 130 μmol) in CH2Cl2 (10 mL) was added dropwise a solution of Bu4NOH (34 mM in CH2Cl2, 5 mL, 175 μmol) over 12 min. The solution was diluted with CH2Cl2 (5mL) and stirred at r.t. for 18 min. The resulting Wittig reaction mixture was introduced into the flow reaction apparatus (Figure 2). The excess Bu4NOH, H2O, and a part of triphenylphosphine oxide in the reaction mixture were trapped with a silica gel column. The solution that flowed out from the column was mixed with the same volume of solution of I2 (16 mg, 64 μmol) in toluene (100 mL) through a ‘T’-shaped connector and irradiated with a 450 W high-pressure mercury arc lamp. The residence time in the photoreaction coil was set to 6 min (cf. Figure 2). The finally obtained reaction solution was concentrated under reduced pressure and the residual crude product was washed with MeOH to afford 1MeCH (24 mg, 78 %). In the above protocol, the products were isolated after washing the crude reaction mixture with MeOH. In some cases, the final products were isolated by column chromatography (Table 1, entries 9 and 18) or recrystallization (Table 1, entry 17).

Reference： [1]Archer, William J.; Taylor, Roger; Gore, Peter H.; Kamounah, Fadhil S. [Journal of the Chemical Society. Perkin transactions II, 1980, # 12, p. 1828 - 1831]
[2]Location in patent: experimental part Scherer, Alexander; Hampel, Frank; Gray, Murray R.; Stryker, Jeffrey M.; Tykwinski, Rik R. [Journal of Physical Organic Chemistry, 2012, vol. 25, # 7, p. 597 - 606]
[3]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

18
[ 23277-00-1 ]
[ 933-88-0 ]
[ 141185-47-9 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium hydroxide In dichloromethane at 20 - 25℃;

Reference： [1]Listvan, V. N.; Stasyuk, A. P.; Kornilov, M. Yu.; Komarov, I. V. [Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 11.2, p. 2168 - 2171][Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 11, p. 2441 - 2445]

19
[ 23277-00-1 ]
[ 6346-05-0 ]
[ 128479-12-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1) diethyl ether, hexane, 5 deg C, 10 min, 2) 4h, roomtemp.; Yield given. Multistep reaction;

Reference： [1]Unterhalt; Dabringhaus [Archiv der Pharmazie, 1990, vol. 323, # 4, p. 253 - 254]

20
[ 23277-00-1 ]
[ 66-77-3 ]
[ 3960-21-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate In ethanol 1.) r.t., 1 h, 2.) r.t., 24 h;
	With potassium hydroxide In dichloromethane; water at 20℃; for 8h;	2-Methylstilbene (typical procedure for Wittig reaction) General procedure: To a mixture of benzyltriphenylphosphonium bromide (14.45 g, 285 mmol) and o-tolaldehyde (3.77 g, 314 mmol) in CH2Cl2 (150 ml) was added aqueous KOH (3.1 g in 5 ml H2O). The mixture was stirred at rt. for 8 h. The organic layer was concentrated under the reduced pressure and the residue was extracted with hexane (100 ml). The extract was successively washed with NaHSO3 aq. and water, then dried (CaCl2). The solvent was evaporated and the residue was chromatographed on silica gel (hexane) to afford 2-methylstilbene (5.21 g, 89%,E : Z ~ 1 : 1). The E/Z product mixture was characterized by 1H NMR spectroscopy by comparison of the spectrum with the reported 1H NMR spectral data [Figure S2 (a)].S2,3
	With tetra(n-butyl)ammonium hydroxide In dichloromethane at 20℃;	Wittig-Mallory Sequential Phenacene Synthesis; Typical Procedure General procedure: To a solution of (1-naphthylmethyl)triphenylphosphonium chloride (55 mg, 125 μmol) and o-tolualdehyde (16 mg, 130 μmol) in CH2Cl2 (10 mL) was added dropwise a solution of Bu4NOH (34 mM in CH2Cl2, 5 mL, 175 μmol) over 12 min. The solution was diluted with CH2Cl2 (5mL) and stirred at r.t. for 18 min. The resulting Wittig reaction mixture was introduced into the flow reaction apparatus (Figure 2). The excess Bu4NOH, H2O, and a part of triphenylphosphine oxide in the reaction mixture were trapped with a silica gel column. The solution that flowed out from the column was mixed with the same volume of solution of I2 (16 mg, 64 μmol) in toluene (100 mL) through a ‘T’-shaped connector and irradiated with a 450 W high-pressure mercury arc lamp. The residence time in the photoreaction coil was set to 6 min (cf. Figure 2). The finally obtained reaction solution was concentrated under reduced pressure and the residual crude product was washed with MeOH to afford 1MeCH (24 mg, 78 %). In the above protocol, the products were isolated after washing the crude reaction mixture with MeOH. In some cases, the final products were isolated by column chromatography (Table 1, entries 9 and 18) or recrystallization (Table 1, entry 17).

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]
[2]Okamoto, Hideki; Takane, Takamitsu; Gohda, Shin; Kubozono, Yoshihiro; Sato, Kaori; Yamaji, Minoru; Satake, Kyosuke [Chemistry Letters, 2014, vol. 43, # 7, p. 994 - 996]
[3]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

21
[ 23277-00-1 ]
[ 66-99-9 ]
[ 10243-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate In ethanol 1.) r.t., 1 h, 2.) r.t., 24 h;

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

22
[ 23277-00-1 ]
[ 146968-47-0 ]
(1S,3S,4S,5R,6R,7R)-6-((4R,6S)-4,6-Dimethyl-octanoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-(6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester [ No CAS ]
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((Z)-4-naphthalen-1-yl-but-3-enyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hexamethylsilazane 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 3 d; Yield given. Multistep reaction. Title compound not separated from byproducts;

Reference： [1]Ponpipom, Mitree M.; Girotra, Narindar N.; Bugianesi, Robert L.; Roberts, Cathleen D.; Berger, Gregory D.; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 23, p. 4031 - 4051]

23
[ 23277-00-1 ]
[ 146968-47-0 ]
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((Z)-4-naphthalen-1-yl-but-3-enyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester [ No CAS ]
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((E)-4-naphthalen-1-yl-but-3-enyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hexamethylsilazane 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 3 d; Yield given. Multistep reaction. Title compound not separated from byproducts;

Reference： [1]Ponpipom, Mitree M.; Girotra, Narindar N.; Bugianesi, Robert L.; Roberts, Cathleen D.; Berger, Gregory D.; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 23, p. 4031 - 4051]

24
[ 23277-00-1 ]
[ 642-31-9 ]
[ 1654-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium ethoxide

Reference： [1]Malkes,L.Ya. et al. [Journal of Organic Chemistry USSR (English Translation), 1965, vol. 1, p. 581 - 583][Zhurnal Organicheskoi Khimii, 1965, vol. 1, # 3, p. 587 - 589]

25
[ 23277-00-1 ]
[ 104-55-2 ]
[ 34662-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In methanol

Reference： [1]Nakabayashi, Kenichi; Arimura, Junichi; Yasuda, Masahide; Shima, Kensuke; Takamuku, Setsuo [Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 5, p. 1313 - 1317]

26
[ 14510-07-7 ]
[ 23277-00-1 ]
4-(2'-naphthalenevinyl)quinolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 8-hydroxyquinoline-4-carbaldehyde; 1-naphthylmethyltriphenylphosphonium chloride With sodium ethanolate In N,N-dimethyl-formamide at 20℃; for 48h; Stage #2: With iodine In toluene for 15h; Heating;

Reference： [1]Chen, Mon-Yao; Hsu, Ming-Ann; Liu, Ching-Yang; Chow, Tahsin J. [Journal of the Chinese Chemical Society, 2004, vol. 51, # 4, p. 735 - 742]

27
[ 23277-00-1 ]
[ 677300-23-1 ]
4-Chloro-7-{(2R,3aS,9aR)-5,5,7,7-tetraisopropyl-3-[1-naphthalen-1-yl-meth-(Z)-ylidene]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With n-butyllithium In tetrahydrofuran at 20℃;

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

28
[ 23277-00-1 ]
[ 83141-42-8 ]
[ 869005-54-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 1-naphthylmethyltriphenylphosphonium chloride With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde In tetrahydrofuran at 20℃; for 10h;

Reference： [1]Gangjee, Aleem; Ye, Zhengqu; Queener, Sherry F. [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1127 - 1133]

29
[ 23277-00-1 ]
(2R,3S,5R)-5-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxymethyl-4-[1-naphthalen-1-yl-meth-(Z)-ylidene]-tetrahydro-furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

30
[ 23277-00-1 ]
(2R,3S,4R,5R)-5-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxymethyl-4-naphthalen-1-ylmethyl-tetrahydro-furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran 4: hydrogen / Pd/C / methanol / 5 h

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

31
[ 23277-00-1 ]
[ 677300-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran 4: 82 percent / hydrogen / Pd/C / methanol / 5 h

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

32
[ 23277-00-1 ]
[ 677300-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran 4: 82 percent / hydrogen / Pd/C / methanol / 5 h 5: pyridine 6: water

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

33
[ 23277-00-1 ]
7-(3-naphthalen-1-ylmethyl-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran 4: 82 percent / hydrogen / Pd/C / methanol / 5 h 5: pyridine

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

34
[ 23277-00-1 ]
N-[7-(3-naphthalen-1-ylmethyl-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran 4: 82 percent / hydrogen / Pd/C / methanol / 5 h 5: pyridine

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

35
[ 23277-00-1 ]
7-{(2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-3-[1-naphthalen-1-yl-meth-(Z)-ylidene]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

36
[ 23277-00-1 ]
[ 677300-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2: NH₃ / dioxane / 96 h / 80 °C 3: tetrabutylammonium fluoride / tetrahydrofuran 4: 82 percent / hydrogen / Pd/C / methanol / 5 h 5: pyridine 6: water 7: 93 percent / Li₂CO₃; 2,6-lutidine / 0 - 20 °C

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

37
[ 23277-00-1 ]
C₄₆H₄₅N₄O₇P*C₆H₁₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 73 percent / n-butyllithium / tetrahydrofuran / 20 °C 2.1: NH₃ / dioxane / 96 h / 80 °C 3.1: tetrabutylammonium fluoride / tetrahydrofuran 4.1: 82 percent / hydrogen / Pd/C / methanol / 5 h 5.1: pyridine 6.1: water 7.1: 93 percent / Li₂CO₃; 2,6-lutidine / 0 - 20 °C 8.1: PCl₃; imidazole / CH₂Cl₂ / -78 - -20 °C 8.2: water

Reference： [1]Madder; Ehrl; Stroemberg [Nucleosides, nucleotides and nucleic acids, 2003, vol. 22, # 5-8, p. 1289 - 1291]

38
[ 23277-00-1 ]
[ 1233-36-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: EtONa / ethanol / 1.) r.t., 1 h, 2.) r.t., 24 h 2: I₂ / o-xylene / 24 h / Heating

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

39
[ 23277-00-1 ]
[ 2633-11-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: EtONa / ethanol / 1.) r.t., 1 h, 2.) r.t., 24 h 2: I₂ / o-xylene / 24 h / Heating

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

40
[ 23277-00-1 ]
[ 159406-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: EtONa / ethanol / 1.) r.t., 1 h, 2.) r.t., 24 h 2: I₂ / o-xylene / 24 h / Heating 3: 94 percent / OsO₄, N-methylmorpholine N-oxide, dihydroquinidine 9-O-(4-chlorobenzoate) / acetone; acetonitrile; H₂O / 23 h / 0 °C

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

41
[ 23277-00-1 ]
(4R,5R)-2,2-Dimethyl-4,5-di-naphthalen-1-yl-[1,3]dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: EtONa / ethanol / 1.) r.t., 1 h, 2.) r.t., 24 h 2: I₂ / o-xylene / 24 h / Heating 3: 94 percent / OsO₄, N-methylmorpholine N-oxide, dihydroquinidine 9-O-(4-chlorobenzoate) / acetone; acetonitrile; H₂O / 23 h / 0 °C 4: 96 percent / p-TsOH, molecular sieves 4 Angstroem / CHCl₃ / 3 h / Heating

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

42
[ 23277-00-1 ]
(S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: EtONa / ethanol / 1.) r.t., 1 h, 2.) r.t., 24 h 2: I₂ / o-xylene / 24 h / Heating 3: OsO₄, N-methylmorpholine N-oxide, dihydroquinidine 9-O-(4-chlorobenzoate) / acetone; acetonitrile; H₂O / 27 h / 0 °C

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

43
[ 23277-00-1 ]
(R,R)-(+)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: EtONa / ethanol / 1.) r.t., 1 h, 2.) r.t., 24 h 2: I₂ / o-xylene / 24 h / Heating 3: OsO₄, N-methylmorpholine N-oxide, dihydroquinidine 9-O-(4-chlorobenzoate) / acetone; acetonitrile; H₂O / 27 h / 0 °C

Reference： [1]Rosini, Carlo; Scamuzzi, Simone; Uccello-Barretta, Gloria; Salvadori, Piero [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7395 - 7400]

44
[ 23277-00-1 ]
(E)-2-tert-Butylsulfanylmethyl-3-naphthalen-2-yl-acrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH (55percent in oil) / 1.) THF, 20 deg C, 4 h; 2.) THF, 35 deg C, 2 h 2: 2N aq. NaOH / ethanol / 5 h / Heating

Reference： [1]Beck; Jendralla; Kammermeier [Tetrahedron, 1994, vol. 50, # 16, p. 4691 - 4698]

45
[ 23277-00-1 ]
[ 156052-61-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH (55percent in oil) / 1.) THF, 20 deg C, 4 h; 2.) THF, 35 deg C, 2 h 2: 2N aq. NaOH / ethanol / 5 h / Heating

Reference： [1]Beck; Jendralla; Kammermeier [Tetrahedron, 1994, vol. 50, # 16, p. 4691 - 4698]

46
[ 23277-00-1 ]
[ 71691-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) n-Bu-Li / 1) diethyl ether, hexane, 5 deg C, 10 min, 2) 4h, roomtemp. 2: 47 percent / natrium, n-butanol 3: 52 percent / 10percent Pd/C / acetic acid / 48 h / Heating

Reference： [1]Unterhalt; Dabringhaus [Archiv der Pharmazie, 1990, vol. 323, # 4, p. 253 - 254]

47
[ 23277-00-1 ]
[ 128479-15-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) n-Bu-Li / 1) diethyl ether, hexane, 5 deg C, 10 min, 2) 4h, roomtemp. 2: 47 percent / natrium, n-butanol

Reference： [1]Unterhalt; Dabringhaus [Archiv der Pharmazie, 1990, vol. 323, # 4, p. 253 - 254]

48
[ 23277-00-1 ]
[ 128479-14-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) n-Bu-Li / 1) diethyl ether, hexane, 5 deg C, 10 min, 2) 4h, roomtemp. 2: 60 percent / H₂ / 10percent Pd/C / acetic acid / 1500.1 - 2250.2 Torr

Reference： [1]Unterhalt; Dabringhaus [Archiv der Pharmazie, 1990, vol. 323, # 4, p. 253 - 254]

49
[ 23277-00-1 ]
[ 108977-33-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiOEt / ethanol 2: (i) hexamethylenetetramine, CHCl₃, (ii) aq. AcOH 3: diethyl ether

Reference： [1]Drefahl,G. et al. [Chemische Berichte, 1961, vol. 94, p. 2002 - 2010]

50
[ 23277-00-1 ]
[ 114305-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: nitrobenzene / Heating

Reference： [1]Zander,M.; Franke,W. [Chemische Berichte, 1961, vol. 94, p. 446 - 450]

51
[ 23277-00-1 ]
[ 121526-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: nitrobenzene / Heating

Reference： [1]Zander,M.; Franke,W. [Chemische Berichte, 1961, vol. 94, p. 446 - 450]

52
[ 23277-00-1 ]
[ 102024-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: LiOEt / ethanol 2: (i) hexamethylenetetramine, CHCl₃, (ii) aq. AcOH 3: diethyl ether 4: (i) SOCl₂, (ii) quinoline
	Multi-step reaction with 3 steps 1: LiOEt / ethanol 2: xylene / Heating 3: LiOEt / ethanol

Reference： [1]Drefahl,G. et al. [Chemische Berichte, 1961, vol. 94, p. 2002 - 2010]
[2]Drefahl,G. et al. [Chemische Berichte, 1961, vol. 94, p. 2002 - 2010]

53
[ 23277-00-1 ]
[ 196-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaOEt / ethanol 2: nitrobenzene / Heating 3: (i) Zn, aq. AcOH, Py, (ii) Cu

Reference： [1]Zander,M.; Franke,W. [Chemische Berichte, 1961, vol. 94, p. 446 - 450]

54
[ 23277-00-1 ]
[ 101936-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiOEt / ethanol 2: (i) hexamethylenetetramine, CHCl₃, (ii) aq. AcOH

Reference： [1]Drefahl,G. et al. [Chemische Berichte, 1961, vol. 94, p. 2002 - 2010]

55
[ 23277-00-1 ]
Triphenyl-<4-(naphthyl-(1)-vinyl)-benzyl>-phosphonium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiOEt / ethanol 2: xylene / Heating

Reference： [1]Drefahl,G. et al. [Chemische Berichte, 1961, vol. 94, p. 2002 - 2010]

56
[ 169504-90-9 ]
[ 23277-00-1 ]
5-hydroxymethyl-4-[cis(naphth-1-yl)ethenyl]-2-n-propyl-l-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hexamethylsilazane In tetrahydrofuran; water; ethyl acetate; toluene; pentane	95.G Part G: Part G: Preparation of 5-hydroxymethyl-4-[cis(naphth-1-yl)ethenyl]-2-n-propyl-l-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole 1-Naphthylmethyltriphenylphosphonium chloride (6.82 g, 0.0155 mol, 2 eq) was suspended in THF (50 mL) and potassium bis(trimethylsilyl)amide (0.75M in toluene, 20.68 mL, 0.0155 mol, 2 eq) was added dropwise thereto at room temperature. The resultant red solution was heated at 450° C. for 0.5 hours. Afterwards, 5-hydroxymethyl-2-n-propyl-l-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole-4-carboxaldehyde (5.00 g, 7.75 mmol, 1 eq) dissolved in a minimum of THF was added at room temperature and allowed to stir overnight. The reaction was worked up by adding 300 mL of ethyl acetate and 200 mL of water. The layers were separated and the organic layer washed with water (2*200 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield 9.29 g of a yellow glass. Flash chromatography in 1:1 pentane/ethyl acetate to 100% ethyl acetate over silica gel yielded 7.95 g of a light yellow glass. NMR (DMSO-d6) δ 8.20-7.20 (m, 20H); 7.10-6.60 (m, 12H); 5.10 (s, 2H); 4.97 (t, 1H, J=7 Hz); 4.00 (m, 2H); 2.20 (t, 2H, J=7 Hz); 0.62 (t, 3H, J=7 Hz). Anal. calcd. for C52 H44 N6 O.(triphenylphosphineoxide)1.6.(H2 O) C, 78.76; H, 5.73; N, 6.82. Found: C, 78.69; H. 5.67; N, 6.90. STR221

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5254546, 1993, A

57
[ 23277-00-1 ]
[ 117613-42-0 ]

Yield	Reaction Conditions	Operation in experiment
8 g (28% from methyl 1-methylisonipecotate)	With hydrogenchloride; sodium methylate In methanol	2 Preparation of 1-methyl-4-(1-naphthylvinyl)piperidine Preparation of 1-methyl-4-(1-naphthylvinyl)piperidine To a mixture of the crude aldehyde and 34.5 g (0.079 mol) of 1-naphthylmethyltriphenylphosphonium chloride in 300 mL of ether was added 22.8 mL (0.1 mol) of 25% sodium methoxide solution in methanol. The orange mixture was stirred for 3 days at ambient temperature, and evaporated. The resulting residue was extracted with 800 mL of hexane. The extract was washed with water (100 mL), dried with magnesium sulfate and evaporated to give a pale yellow semisolid. The semisolid was dissolved in 500 mL of ether. Dry hydrogen chloride was bubbled through the ethereal solution to precipitate a white solid. The solid was collected by filtration and recrystallized from ethanol-ether (or isopropyl alcohol-ethyl acetate) to give 8 g (28% from methyl 1-methylisonipecotate) of 1-methyl-4-(1-naphthylvinyl)piperidine hydrochloride (B-120): mp 196°-199° C. NMR d(CD3 OC) δ1.75-1.91 (m, 2H), 2.09-2.30 (m, 2H), 2.55-2.70 (br, 1H), 2.91 (s, 3H), 3.00-3.20 (m, 2H), 3.48-3.66 (m, 2H), 6.20 (dd, 1H, J=7 Hz and 16 Hz), 7.28 (d, 1H, J=16 Hz), 7.36-7.61 (m, 4H), 7.73-7.89 (m, 2H), 8.07-8.16 (m, 1H). IR: 2950, 2680, 2550, 1740, 1460, 14410, 1250, 1040, 950 and 780 cm-1. Anal. Calcd for C18 H22 NCl.1/2 H2 O: C, 72.85; H, 7.76; N, 4.72. Found: C, 72.46; H, 7.90; N, 484.

Reference： [1]Current Patent Assignee: DYNAMAC; DYANAMAC - US4757079, 1988, A

58
5-methyl-4-(4-methylpiperidino)-2-pyridinecarbaldehyde [ No CAS ]
[ 23277-00-1 ]
5-methyl-4-(4-methylpiperidino)-2-[2-(1-naphthyl)ethyl]pyridine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; hexane; water	62 EXAMPLE 62 EXAMPLE 62 Production of 5-methyl-4-(4-methylpiperidino)-2-[2-(1-naphthyl)ethyl]pyridine hydrochloride: A suspension of 6.6 g (15.0 mmoles) of (1-naphthylmethyl)triphenylphosphonium chloride in 40 ml of tetrahydrofuran was cooled to about -30° C. in a cooling bath, and under a nitrogen stream, 12.6 ml of 1.55M n-butyllithium in hexane was added dropwise. The reaction mixture was further stirred at the above temperature for 0.5 hour and further a solution of 2.7 g (12.4 mmoles) of 5-methyl-4-(4-methylpiperidino)-2-pyridinecarbaldehyde in 10 ml of tetrahydrofuran was added dropwise. After the addition the cooling bath was removed and the temperature was raised to room temperature. The mixture was further stirred at room temperature for 2 hours. Water (60 ml) was added to the reaction mixture, and tetrahydrofuran was evaporated under-reduced pressure. The remaining aqueous layer was extracted with hexane. The hexane layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting oily product was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate=3/1) to give a mixture of (Z)- and (E)-5-methyl-4-(4-methylpiperidino)-2-[2-(1-naphthyl)vinyl]-pyridines as an oil.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US4839353, 1989, A

59
[ 939-97-9 ]
[ 23277-00-1 ]
1-((Z)-4-tert-butylstyryl)naphthalene [ No CAS ]
(E)-1-(4'-t-butylstyryl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-naphthylmethyltriphenylphosphonium chloride With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 4-tert-Butylbenzaldehyde In tetrahydrofuran at 20℃; for 24.75h;	2.a Example 2This example illustrates the preparation of Compound E2, 3-fe/t-butyl-N6,N6,N12,N12-tetrakis(3,4-dimethylphenyl)-chrysene-6,12- diaminea. Preparation of 1 -(4-te/t-butylstyryl)naphthalenes. An oven-dried 500 ml three-neck round bottom flask was equipped with a magnetic stir bar, addition funnel and nitrogen inlet connector. The flask was charged with (i-napthylmethyl)triphenylphosphonium chloride (12.07 g, 27.5 mmol) and 200 ml of anhydrous THF. Sodium hydride (1.1 g, 25 mmol) was added in one portion. The mixture became bright orange and was left to stir overnight at room temperature. A solution of 4-tert- butyl-benzaldehyde (7.1 g, 25 mmol) in anhydrous THF (30ml) was added to the addition funnel with a cannula. The aldehyde solution was added to the reaction mixture dropwise over 45 minutes. Reaction was left to stir at room temperature for 24 hours (orange color went away). Silica gel was added to the reaction mixture and volatiles were removed under reduced pressure. The crude product was purified by column chromatography on silica gel using 5-10 % dichloromethane in hexanes. The product was isolated as a mixture of cis- and trans-isomers (6.3 g, 89 %) and used without separation. 1H NMR (CD2CI2): δ 1.27 (s, 9H), 7.08 (d, 1 H, J = 16 Hz), 7.33-7.49 (m, 7H), 7.68 (d, 1 H, J = 7.3 Hz), 7.71 (d, 1 H, J = 8.4 Hz), 7.76-7.81 (m, 2H), 8.16 (d, 1 H, J = 8.3 Hz).

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2008/147721, 2008, A1 Location in patent: Page/Page column 25

60
[ 23277-00-1 ]
NTPPPODS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With dipotassium peroxodisulfate In water at 20℃; for 0.333333h;

Reference： [1]Location in patent: experimental part Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Ramzanian-Lehmali, Farhad [Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 6, p. 1388 - 1395]

61
[ 869901-02-0 ]
[ 23277-00-1 ]
[ 1220713-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-naphthylmethyltriphenylphosphonium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)tetrahydro-1(2H)-pyridinecarboxylate In tetrahydrofuran at 0 - 20℃; for 0.833333h; Stage #3: With water; ammonium chloride In tetrahydrofuran	tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (IV-3) tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (IV-3) Under argon, (1-naphthylmethyl)triphenylphosphonium chloride (2.96 g) is dissolved in 20 ml of tetrahydrofuran and cooled to 0° C., and potassium tert.-butoxide (757 mg) is added, whereupon the colour of the solution changes to dark-red. After 10 min of stirring, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.00 g) is added. The mixture is stirred at 0° C. for another 30 min and then slowly warmed to room temperature. After a further 20 min, saturated ammonium chloride solution is added, and the aqueous phase is separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.2 g, Z isomer). 1H NMR (DMSO-d6): δ 7.92 (t, 2H), 7.87-7.80 (m, 1H), 7.50-7.48 (m, 4H), 7.10 (d, 1H), 6.91 (d, 1H), 6.86 (s, 1H), 3.75 (d, 2H), 2.98 (m, 1H), 2.80 (t, 2H), 1.80-1.70 (m, 2H), 1.40 (s, 9H), 1.30 (qd, 2H) ppm MS (ESI): 421 ([M+H]+)

Reference： [1]Current Patent Assignee: BAYER AG - US2010/137245, 2010, A1 Location in patent: Page/Page column 35-36

62
[ 939-97-9 ]
[ 23277-00-1 ]
(E)-1-(4'-t-butylstyryl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; dichloromethane	C.A.a Comparative Example A (a) Preparation of 1-(4-tert-butylstyryl)naphthalene. An oven-dried 500 ml three-neck round bottom flask was equipped with a magnetic stir bar, addition funnel and nitrogen inlet connector. The flask was charged with (1-napthylmethyl)triphenylphosphonium chloride (12.07 g, 27.5 mmol) and 200 ml of anhydrous THF. Sodium hydride (1.1 g, 25 mmol) was added in one portion. The mixture became bright orange and was left to stir overnight at room temperature. A solution of 4-tert-butyl-benzaldehyde (7.1 g, 25 mmol) in anhydrous THF (30 ml) was added to the addition funnel with a cannula. The aldehyde solution was added to the reaction mixture dropwise over 45 minutes. Reaction was left to stir at room temperature for 24 hours (orange color went away). Silica gel was added to the reaction mixture and volatiles were removed under reduced pressure. The crude product was purified by column chromatography on silica gel using 5-10% dichloromethane in hexanes. The product was isolated as a mixture of cis- and trans-isomers (6.3 g, 89%) and used without separation. The structure was confirmed by 1H NMR.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US2010/187983, 2010, A1

63
[ 23277-00-1 ]
[ 1333015-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere

Reference： [1]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]

64
[ 23277-00-1 ]
[ 1333015-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere 3: decalin / 119.4 °C

Reference： [1]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]
[2]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]

65
[ 23277-00-1 ]
[ 1361948-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere

Reference： [1]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]

66
[ 23277-00-1 ]
[ 1361949-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere

Reference： [1]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]

67
[ 23277-00-1 ]
[ 1333015-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere 3: 1.5 h / 200 °C / Inert atmosphere; Neat (no solvent)
	Multi-step reaction with 4 steps 1: sodium ethanolate / ethanol / Inert atmosphere 2: ethanol / 14 h / 20 °C / Inert atmosphere 3: decalin / 119.4 °C 4: 1.5 h / 200 °C / Inert atmosphere; Neat (no solvent)

Reference： [1]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]
[2]Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]

68
[ 23277-00-1 ]
[ 60824-80-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate In ethanol Inert atmosphere;

Reference： [1]Location in patent: experimental part Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner [Helvetica Chimica Acta, 2011, vol. 94, # 8, p. 1359 - 1388]

69
[ 23277-00-1 ]
N-(4-(2-(1-naphthalenyl)ethyl)phenylmethylene)-2-naphthalenamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium hydroxide monohydrate / isopropyl alcohol / 0.33 h 1.2: 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / toluene / 48 h / 62059.4 Torr / Autoclave 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 16 h / -78 - 20 °C / Inert atmosphere 4.1: toluene / 16 h / Reflux

Reference： [1]Scherer, Alexander; Hampel, Frank; Gray, Murray R.; Stryker, Jeffrey M.; Tykwinski, Rik R. [Journal of Physical Organic Chemistry, 2012, vol. 25, # 7, p. 597 - 606]

70
[ 23277-00-1 ]
[ 1384485-12-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: lithium hydroxide monohydrate / isopropyl alcohol / 0.33 h 1.2: 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / toluene / 48 h / 62059.4 Torr / Autoclave 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 16 h / -78 - 20 °C / Inert atmosphere 4.1: toluene / 16 h / Reflux 5.1: hydrogenchloride / ethanol; water / 16 h / Reflux

Reference： [1]Scherer, Alexander; Hampel, Frank; Gray, Murray R.; Stryker, Jeffrey M.; Tykwinski, Rik R. [Journal of Physical Organic Chemistry, 2012, vol. 25, # 7, p. 597 - 606]

71
[ 23277-00-1 ]
[ 1384485-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / isopropyl alcohol / 0.33 h 1.2: 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / toluene / 48 h / 62059.4 Torr / Autoclave 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 16 h / -78 - 20 °C / Inert atmosphere

Reference： [1]Scherer, Alexander; Hampel, Frank; Gray, Murray R.; Stryker, Jeffrey M.; Tykwinski, Rik R. [Journal of Physical Organic Chemistry, 2012, vol. 25, # 7, p. 597 - 606]

72
[ 23277-00-1 ]
[ 75612-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium hydroxide monohydrate / isopropyl alcohol / 0.33 h 1.2: 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / toluene / 48 h / 62059.4 Torr / Autoclave

Reference： [1]Scherer, Alexander; Hampel, Frank; Gray, Murray R.; Stryker, Jeffrey M.; Tykwinski, Rik R. [Journal of Physical Organic Chemistry, 2012, vol. 25, # 7, p. 597 - 606]

73
[ 23277-00-1 ]
[ 218-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / dichloromethane; water / 8 h / 20 °C 2: iodine / cyclohexane / 0.1 h / Irradiation
	Multi-step reaction with 2 steps 1: tetra(n-butyl)ammonium hydroxide / dichloromethane / 20 °C 2: iodine / dichloromethane / 0.1 h / Irradiation; Flow reactor

Reference： [1]Okamoto, Hideki; Takane, Takamitsu; Gohda, Shin; Kubozono, Yoshihiro; Sato, Kaori; Yamaji, Minoru; Satake, Kyosuke [Chemistry Letters, 2014, vol. 43, # 7, p. 994 - 996]
[2]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

74
[ 23277-00-1 ]
[ 3351-28-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / dichloromethane; water / 8 h / 20 °C 2: iodine / cyclohexane / 0.1 h / Irradiation
	Multi-step reaction with 2 steps 1: tetra(n-butyl)ammonium hydroxide / dichloromethane / 20 °C 2: iodine / dichloromethane / 0.1 h / Irradiation; Flow reactor

Reference： [1]Okamoto, Hideki; Takane, Takamitsu; Gohda, Shin; Kubozono, Yoshihiro; Sato, Kaori; Yamaji, Minoru; Satake, Kyosuke [Chemistry Letters, 2014, vol. 43, # 7, p. 994 - 996]
[2]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

75
[ 23277-00-1 ]
[ 100-52-7 ]
1-styrylnaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In dichloromethane; water at 20℃; for 8h;	2-Methylstilbene (typical procedure for Wittig reaction) General procedure: To a mixture of benzyltriphenylphosphonium bromide (14.45 g, 285 mmol) and o-tolaldehyde (3.77 g, 314 mmol) in CH2Cl2 (150 ml) was added aqueous KOH (3.1 g in 5 ml H2O). The mixture was stirred at rt. for 8 h. The organic layer was concentrated under the reduced pressure and the residue was extracted with hexane (100 ml). The extract was successively washed with NaHSO3 aq. and water, then dried (CaCl2). The solvent was evaporated and the residue was chromatographed on silica gel (hexane) to afford 2-methylstilbene (5.21 g, 89%,E : Z ~ 1 : 1). The E/Z product mixture was characterized by 1H NMR spectroscopy by comparison of the spectrum with the reported 1H NMR spectral data [Figure S2 (a)].S2,3
	With tetra(n-butyl)ammonium hydroxide In dichloromethane at 20℃;	Wittig-Mallory Sequential Phenacene Synthesis; Typical Procedure General procedure: To a solution of (1-naphthylmethyl)triphenylphosphonium chloride (55 mg, 125 μmol) and o-tolualdehyde (16 mg, 130 μmol) in CH2Cl2 (10 mL) was added dropwise a solution of Bu4NOH (34 mM in CH2Cl2, 5 mL, 175 μmol) over 12 min. The solution was diluted with CH2Cl2 (5mL) and stirred at r.t. for 18 min. The resulting Wittig reaction mixture was introduced into the flow reaction apparatus (Figure 2). The excess Bu4NOH, H2O, and a part of triphenylphosphine oxide in the reaction mixture were trapped with a silica gel column. The solution that flowed out from the column was mixed with the same volume of solution of I2 (16 mg, 64 μmol) in toluene (100 mL) through a ‘T’-shaped connector and irradiated with a 450 W high-pressure mercury arc lamp. The residence time in the photoreaction coil was set to 6 min (cf. Figure 2). The finally obtained reaction solution was concentrated under reduced pressure and the residual crude product was washed with MeOH to afford 1MeCH (24 mg, 78 %). In the above protocol, the products were isolated after washing the crude reaction mixture with MeOH. In some cases, the final products were isolated by column chromatography (Table 1, entries 9 and 18) or recrystallization (Table 1, entry 17).

Reference： [1]Okamoto, Hideki; Takane, Takamitsu; Gohda, Shin; Kubozono, Yoshihiro; Sato, Kaori; Yamaji, Minoru; Satake, Kyosuke [Chemistry Letters, 2014, vol. 43, # 7, p. 994 - 996]
[2]Okamoto, Hideki; Takahashi, Haruhiko; Takane, Takamitsu; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Gohda, Shin; Yamaji, Minoru [Synthesis, 2017, vol. 49, # 13, p. 2949 - 2957]

76
[ 23277-00-1 ]
[ 529-20-4 ]
(E)-1-(2-methylphenyl)-2-(1-naphthyl)ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In dichloromethane; water at 20℃; for 8h;	2-Methylstilbene (typical procedure for Wittig reaction) General procedure: To a mixture of benzyltriphenylphosphonium bromide (14.45 g, 285 mmol) and o-tolaldehyde (3.77 g, 314 mmol) in CH2Cl2 (150 ml) was added aqueous KOH (3.1 g in 5 ml H2O). The mixture was stirred at rt. for 8 h. The organic layer was concentrated under the reduced pressure and the residue was extracted with hexane (100 ml). The extract was successively washed with NaHSO3 aq. and water, then dried (CaCl2). The solvent was evaporated and the residue was chromatographed on silica gel (hexane) to afford 2-methylstilbene (5.21 g, 89%,E : Z ~ 1 : 1). The E/Z product mixture was characterized by 1H NMR spectroscopy by comparison of the spectrum with the reported 1H NMR spectral data [Figure S2 (a)].S2,3

Reference： [1]Okamoto, Hideki; Takane, Takamitsu; Gohda, Shin; Kubozono, Yoshihiro; Sato, Kaori; Yamaji, Minoru; Satake, Kyosuke [Chemistry Letters, 2014, vol. 43, # 7, p. 994 - 996]

77
[ 23277-00-1 ]
C₂₇H₁₇BF₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium hydroxide / chloroform 2: benzene 3: iodine; oxygen / cyclohexane / Photolysis; Flow reactor 4: chloral hydrate / hexane; dichloromethane 5: sodium hydride / tetrahydrofuran 6: benzene