(3E,13Z)-十八碳二烯-1-基乙酸酯合成路线 （共 61 条）
反应条件
1: 96 percent / NaBr / dimethylformamide / 1 h / 50 °C
3: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C
4: 100 percent / MeSiBr / ZnBr / CH2Cl2 / 0.33 h / 0 °C
5: 89 percent / dibenzo-18-crown-6 / acetonitrile / 15 h / Heating
View Scheme
参考文献
Moiseenkov, Alexander M.; Czeskis, Boris A.; Ivanova, Natalya M.; Nefedov, Oleg M.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , p. 2639 - 2649
反应条件
sodium ethanolate in toluene
T=25°C; 2 h; Yield given. Yields of byproduct given;
参考文献
Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos; Szantay, Csaba
Acta Chimica Hungarica, 1988 , vol. 125, # 6 p. 797 - 820
反应条件
1: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h
2: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C
3: 58 percent / LAH / bis-(2-methoxy-ethyl) ether / 48 h / Heating
4: 81 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature
View Scheme
参考文献
Singh, Vasundhara; Trehan, I. R.; Kad, G. L.
Journal of the Indian Chemical Society, 1992 , vol. 69, # 2 p. 103 - 105
反应条件
1: 1.) NaNH2, HMPA / 1.) THF, RT, 90 min, 2.) THF, from -78 deg C to RT, 5 h
2: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature
3: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h
4: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C
5: 58 percent / LAH / bis-(2-methoxy-ethyl) ether / 48 h / Heating
6: 81 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature
View Scheme
参考文献
Singh, Vasundhara; Trehan, I. R.; Kad, G. L.
Journal of the Indian Chemical Society, 1992 , vol. 69, # 2 p. 103 - 105
参考文献
Syntex (U.S.A.) Inc.
Patent: US4296042 A1, 1981 ;
反应条件
1: 90 percent / acetonitrile / 24 h / Heating
2: NaOEt / tetrahydrofuran / 1 h / 25 °C
3: NaOEt / toluene / 2 h / 25 °C
4: PBr3
5: 98 percent / acetonitrile / 24 h / Heating
6: NaOEt / tetrahydrofuran / 1 h / 25 °C
7: n-BuLi / toluene / 2 h / 25 °C
View Scheme
参考文献
Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos; Szantay, Csaba
Acta Chimica Hungarica, 1988 , vol. 125, # 6 p. 797 - 820
反应条件
1: NaOEt / toluene / 2 h / 25 °C
2: PBr3
3: 98 percent / acetonitrile / 24 h / Heating
4: NaOEt / tetrahydrofuran / 1 h / 25 °C
5: n-BuLi / toluene / 2 h / 25 °C
View Scheme
参考文献
Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos; Szantay, Csaba
Acta Chimica Hungarica, 1988 , vol. 125, # 6 p. 797 - 820
反应条件
1: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h
2: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h
3: Dowex W-50 (H+ form) / methanol / 16 h
4: 66 percent / sodium, 1,2-ethanediol / toluene / 2 h / 98 - 100 °C
5: pyridine
View Scheme
参考文献
Hoskovec, Michal; Saman, David; Koutek, Bohumir
Collection of Czechoslovak Chemical Communications, 1990 , vol. 55, # 9 p. 2270 - 2281
反应条件
1: 54 percent / piperidine, acetic acid / xylene / Heating
2: 80 percent / LiAlH4 / diethyl ether / 1 h / 20 - 22 °C
3: 88.5 percent / pyridine / benzene
View Scheme
参考文献
Sorochinskaya, A.M.; Kovalev, B.G.
Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 4.1 p. 621 - 624
Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 4 p. 722 - 727
反应条件
1: 80 percent / LiAlH4 / diethyl ether / 1 h / 20 - 22 °C
2: 88.5 percent / pyridine / benzene
View Scheme
参考文献
Sorochinskaya, A.M.; Kovalev, B.G.
Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 4.1 p. 621 - 624
Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 4 p. 722 - 727
