(Z,E)-十三-4,7-二烯-1-醇合成路线 （共 44 条）
反应条件
1: 1.) C2H5MgBr, 2.) cuprous chloride / 1.) THF, reflux, 3 h, 2.) a). 20 deg C, 2 h, b). 65 deg C, 12 h
2: 98 percent / ammonium sulfate, tert-butyl alcohol, lithium / tetrahydrofuran; liquid ammonia / 2 h
View Scheme
参考文献
Ishchenko, R. I.; Kovalev, B. G.
Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 2.1 p. 258 - 262
Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 2 p. 291 - 296
反应条件
1: 2.) BF3*2AcOH / 1.) NH3(liquid), 2 h, 2.) from 40 to 45 deg C, 20 h
2: 78 percent / conc. HCl / methanol / 4 h
3: 1.) H2, 2.) PBr3 / 1.) NIP-2 / 2.) ether, reflux, 4 h
4: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h
5: 79 percent / conc. H2SO4 / CCl4 / 10 h
6: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C
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参考文献
Gocan, Alexandra; Gansca, Lucia; Oprean, Ioan
Revue Roumaine de Chimie, 1995 , vol. 40, # 3 p. 253 - 258
反应条件
1: 83 percent / tetrahydrofuran
2: 74 percent / H2 / (methyl benzoate)chromium tricarbonyl / acetone / 3 h / 120 - 125 °C / 45600 Torr
3: 71 percent / propionic acid / toluene / 3 h / Heating
4: 76 percent / LiAlH4 / diethyl ether
View Scheme
参考文献
Vasil'ev; Serebryakov
Russian Chemical Bulletin, 1996 , vol. 45, # 9 p. 2232 - 2235
反应条件
1: 74 percent / H2 / (methyl benzoate)chromium tricarbonyl / acetone / 3 h / 120 - 125 °C / 45600 Torr
2: 71 percent / propionic acid / toluene / 3 h / Heating
3: 76 percent / LiAlH4 / diethyl ether
View Scheme
参考文献
Vasil'ev; Serebryakov
Russian Chemical Bulletin, 1996 , vol. 45, # 9 p. 2232 - 2235
反应条件
1: 78 percent / conc. HCl / methanol / 4 h
2: 1.) H2, 2.) PBr3 / 1.) NIP-2 / 2.) ether, reflux, 4 h
3: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h
4: 79 percent / conc. H2SO4 / CCl4 / 10 h
5: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C
View Scheme
参考文献
Gocan, Alexandra; Gansca, Lucia; Oprean, Ioan
Revue Roumaine de Chimie, 1995 , vol. 40, # 3 p. 253 - 258
反应条件
1: 1) LiNH2 / 1) liq.NH3, -33 deg C, 2 h, 2) THF, -33 deg C, 0.5 h
2: 65 percent / propionic acid / 2 h / 138 °C
3: 80 percent / H2, quinoline / Pd-CaCO3 / hexane / 760 Torr
4: 98 percent / LiAlH4 / diethyl ether / 2 h
View Scheme
参考文献
Yadav, J. S.; Kulkarni, A. D.; Reddy, P. Satyanarayana
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986 , vol. 25, p. 1220 - 1223
反应条件
1: 85 percent / hydrogen, triethylamine / P(2)-Ni / ethanol
2: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating
3: 83 percent / propionic acid / 1 h / 140 °C
4: LiAlH4 / diethyl ether
View Scheme
参考文献
Chattopadhyay, A.; Mamdapur, V. R.; Chadha, M. S.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, # 1-12 p. 187 - 188
反应条件
1: conc. H2SO4 / CCl4 / Heating
2: LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 20 h / 145 - 150 °C
View Scheme
参考文献
Gansca, Lucia; Gocan, Alexandra; Oprean, Ioan; Maxim, Sanda; Budae, Iuliana
Revue Roumaine de Chimie, 2001 , vol. 46, # 11 p. 1243 - 1248
反应条件
1: 85 percent / PBr3, pyridine / diethyl ether / 12 h / Ambient temperature
2: 1.) LiNH2, liquid NH3 / 1.) THF, 2 h, 2.) 20 min
3: 90 percent / Na, liquid NH3 / tetrahydrofuran / 1 h
View Scheme
参考文献
Yadav, J. S.; Reddy, P. Satyanarayana
Synthetic Communications, 1986 , vol. 16, # 9 p. 1119 - 1132
反应条件
1: 90 percent / liquid NH3, Li / 2 h
2: 85 percent / PBr3, pyridine / diethyl ether / 12 h / Ambient temperature
3: 1.) LiNH2, liquid NH3 / 1.) THF, 2 h, 2.) 20 min
4: 90 percent / Na, liquid NH3 / tetrahydrofuran / 1 h
View Scheme
参考文献
Yadav, J. S.; Reddy, P. Satyanarayana
Synthetic Communications, 1986 , vol. 16, # 9 p. 1119 - 1132
