(E)-11-十六碳烯醛合成路线 （共 13 条）
反应条件
oxalyl dichloride; dimethyl sulfoxide in dichloromethane
T=-60°C; 0.25 h;
参考文献
Brown, Herbert C.; Lee, Hsiupu D.; Kulkarni, Surendra U.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5282 - 5286
反应条件
1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane
T=-78°C; 0.25 h;
2: With triethylamine in dichloromethane
Overall yield = 95 percent; Overall yield = 0.20 g;
参考文献
GRUBBS, ROBERT H.; HERBERT, MYLES B.; WICKENS, ZACHARY K.; MARX, VANESSA M.
Patent: US2013/231499 A1, 2013 ;
Location in patent: Paragraph 0181; 0182 ;
反应条件
1: 1.) ThxBHCl*Me2S, 2.) KIPBH, 3.) NaOMe, 4.) AcOH
2: 97 percent / 20percent aq. NaOH / aq. ethanol / 0.5 h / Ambient temperature
3: 98 percent / oxalyl chloride, Me2SO / CH2Cl2 / 0.25 h / -60 °C
View Scheme
参考文献
Brown, Herbert C.; Lee, Hsiupu D.; Kulkarni, Surendra U.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5282 - 5286
反应条件
1: 1.) ThxBHCl*Me2S, 2.) KIPBH, 3.) NaOMe, 4.) AcOH
2: 97 percent / 20percent aq. NaOH / aq. ethanol / 0.5 h / Ambient temperature
3: 98 percent / oxalyl chloride, Me2SO / CH2Cl2 / 0.25 h / -60 °C
View Scheme
参考文献
Brown, Herbert C.; Lee, Hsiupu D.; Kulkarni, Surendra U.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5282 - 5286
反应条件
1: 97 percent / 20percent aq. NaOH / aq. ethanol / 0.5 h / Ambient temperature
2: 98 percent / oxalyl chloride, Me2SO / CH2Cl2 / 0.25 h / -60 °C
View Scheme
参考文献
Brown, Herbert C.; Lee, Hsiupu D.; Kulkarni, Surendra U.
Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5282 - 5286
反应条件
1: 1) Mg, 2) Li2CuCl4 / 1) THF, 2) THF, a) -70 deg C to 20 deg C over 45 min, b) 2 h at 20 deg C
2: 92 percent / TsOH*Py / methanol / 3 h / 45 °C
3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Cheskis, B. A.; Ivanova, N. M.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990 , vol. 39, # 11 p. 2296 - 2300
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990 , # 11 p. 2539 - 2544
反应条件
1: 1.) lithium amide / 1.) HMPTA, RT, 1.5 h, 2.) HMPTA, 25 deg C, 8 h
2: 56.3 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 48 h / 140 °C
3: 85 percent / pyridinium chlorochromate / CH2Cl2 / 20 - 25 °C
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: 56.3 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 48 h / 140 °C
2: 85 percent / pyridinium chlorochromate / CH2Cl2 / 20 - 25 °C
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: 1.) lithium amide / 1.) HMPTA, RT, 1.5 h, 2.) HMPTA, 25 deg C, 8 h
2: 56.3 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 48 h / 140 °C
3: 85 percent / pyridinium chlorochromate / CH2Cl2 / 20 - 25 °C
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: 1) Mg, 2) Li2CuCl4 / 1) THF, 2) THF, a) -70 deg C to 20 deg C over 45 min, b) 2 h at 20 deg C
2: 92 percent / TsOH*Py / methanol / 3 h / 45 °C
3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Cheskis, B. A.; Ivanova, N. M.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990 , vol. 39, # 11 p. 2296 - 2300
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990 , # 11 p. 2539 - 2544
