2-[(三甲基硅基)乙炔基]苯甲醛合成路线 （共 35 条）
反应条件
1: With gallium(III) chloride in dichloromethane T=-78°C; chelation; 0.5 h; 2: With triphenylstannane T=-78°C; Reduction; 1 h; Further stages.;
参考文献
Asao, Naoki; Asano, Toru; Ohishi, Takeshi; Yamamoto, Yoshinori
Journal of the American Chemical Society, 2000 , vol. 122, # 19 p. 4817 - 4818
反应条件
1.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C 1.2: 0.5 h / 0 - 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.17 h / -78 °C / |Inert atmosphere View Scheme
参考文献
Nobusue, Shunpei; Mukai, Yuichi; Fukumoto, Yo; Umeda, Rui; Tahara, Kazukuni; Sonoda, Motohiro; Tobe, Yoshito
Chemistry--A European Journal, 2012 , vol. 18, # 40 p. 12814 - 12824,11
反应条件
1.1: t-BuOK / tetrahydrofuran / 1 h / 0 °C
1.2: tetrahydrofuran / 16 h / 20 °C
2.1: K2CO3 / methanol / 2 h
View Scheme
参考文献
Madhushaw, Reniguntala J.; Lin, Ming-Yuan; Abu Sohel, Shariar Md.; Liu, Rai-Shung
Journal of the American Chemical Society, 2004 , vol. 126, # 22 p. 6895 - 6899
反应条件
1: triphenylbenzyl-phosphonium bromide With n-butyllithium in tetrahydrofuran
T=0°C; 0.5 h;
2: 2-(2-trimethylsilyleth-1-yn-1-yl)benzaldehyde in tetrahydrofuran
T=20°C; 4 h;
参考文献
Madhushaw, Reniguntala J.; Lin, Ming-Yuan; Abu Sohel, Shariar Md.; Liu, Rai-Shung
Journal of the American Chemical Society, 2004 , vol. 126, # 22 p. 6895 - 6899
反应条件
1: Ph3P=CHPh With potassium tert-butylate in tetrahydrofuran
T=0°C; 1 h;
2: 2-(2-trimethylsilyleth-1-yn-1-yl)benzaldehyde in tetrahydrofuran
T=20°C; 16 h; Further stages.;
参考文献
Barluenga, Jose; Andina, Facundo; Aznar, Fernando; Valde, Carlos
Organic Letters, 2007 , vol. 9, # 21 p. 4143 - 4146
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / |Inert atmosphere
1.2: 1 h / -78 - 28 °C / |Inert atmosphere
2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere
2.2: 1.5 h / 0 °C / |Inert atmosphere
3.1: potassium carbonate / methanol; dichloromethane / 1 h / 20 °C
4.1: [(C6F5)3P]AuCl; silver hexafluoroantimonate / nitromethane / 4 h / 28 °C / |Inert atmosphere
View Scheme
参考文献
Wang, Chiou-Dong; Hsieh, Yi-Feng; Liu, Rai-Shung
Advanced Synthesis and Catalysis, 2014 , vol. 356, # 1 p. 144 - 152
反应条件
1.1: n-BuLI / tetrahydrofuran / 0.5 h / 0 °C
1.2: tetrahydrofuran / 4 h / 20 °C
2.1: Bu4NF / tetrahydrofuran / 8 h / 26 °C
View Scheme
参考文献
Chen, Chun-Hao; Tsai, Yen-Ching; Liu, Rai-Shung
Angewandte Chemie - International Edition, 2013 , vol. 52, # 17 p. 4599 - 4603
Angew. Chem., 2013 , p. 4697 - 4701,5
反应条件
1.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C
1.2: tetrahydrofuran / 4 h / 20 °C
2.1: Bu4NF / tetrahydrofuran / 8 h / 26 °C
View Scheme
参考文献
Madhushaw, Reniguntala J.; Lin, Ming-Yuan; Abu Sohel, Shariar Md.; Liu, Rai-Shung
Journal of the American Chemical Society, 2004 , vol. 126, # 22 p. 6895 - 6899
反应条件
1: [i-PrPPh3](+)Br(-) With n-butyllithium in tetrahydrofuran
T=0°C; 0.5 h; Inert atmosphere;
2: 2-(2-trimethylsilyleth-1-yn-1-yl)benzaldehyde in tetrahydrofuran
T=0 - 20°C; Wittig reaction; 4 h; Inert atmosphere;
参考文献
Lopez-Carrillo, Veronica; Huguet, Nuria; Mosquera, Ungeles; Echavarren, Antonio M.
Chemistry - A European Journal, 2011 , vol. 17, # 39 p. 10972 - 10978
反应条件
1: isopropyl-triphenyl-phosphonium iodide With n-butyllithium in tetrahydrofuran
T=0°C; 0.5 h; Inert atmosphere;
2: 2-(2-trimethylsilyleth-1-yn-1-yl)benzaldehyde in tetrahydrofuran
T=0°C; 1 h; Inert atmosphere;
参考文献
Chen, Chun-Hao; Tsai, Yen-Ching; Liu, Rai-Shung
Angewandte Chemie - International Edition, 2013 , vol. 52, # 17 p. 4599 - 4603
Angew. Chem., 2013 , p. 4697 - 4701,5
