2-(6-溴己氧基)四氢-2H-吡喃合成路线 （共 75 条）
反应条件
1: 1.) Mg / 1.) THF, RT, 1 h, 2.) overnight
2: 66.1 percent / pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1 h / Ambient temperature
3: 78.1 percent / PTS / methanol / 6 h / Ambient temperature
View Scheme
参考文献
Vig; Sharma; Walia; Thaper
Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990 , vol. 29, # 8 p. 760 - 762
反应条件
1: 1.) BuLi / 1.) THF, hexane, 2 h, -20 deg C, 2.) 30 min, -78 degC
2: LiAlH4 / diethyl ether / 1 h / 0 °C
3: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating
View Scheme
参考文献
Canevet; Roeder; Vostrowsky; Bestmann
Chemische Berichte, 1980 , vol. 113, # 3 p. 1115 - 1120
反应条件
1: 1) Mg, 2) Li2CuCl4 / 1) THF, 2) THF, -70 deg C to 20 deg C
2: 97 percent / TsOH*Py / methanol / 45 °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: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
dilithium tetrachlorocuprate in tetrahydrofuran
T=-78°C; 4 h;
参考文献
Hassarajani, S. A.; Mithran, S.; Mamdapur, V. R.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 5 p. 429 - 431
反应条件
LAETA
1.) benzene, hexane, 10 deg C, 5 min, 2.) THF, benzene, hexane, RT; Yield given. Multistep reaction. Yields of byproduct given;
参考文献
Balova, I. A.; Remizova, L. A.; Makarycheva, V. F.; Rumyantseva, E. G.; Favorskaya, I. A.
Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 1 p. 55 - 57
Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 1 p. 64 - 66
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
3.1: sulfuric acid / 20 °C
4.1: hydrogen; ethylenediamine / ethanol; water
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
1.1: magnesium / tetrahydrofuran
1.2: 79 percent / dilithium tetrachlorocuprate / tetrahydrofuran / -78 - 20 °C
2.1: 97 percent / p-toluenesulfonic acid monohydrate / ethanol / 3 h / Heating
3.1: 74 percent / Jones' CrO3 reagent / acetone / 0 - 20 °C
View Scheme
参考文献
Masuda, Yui; Yoshida, Masao; Mori, Kenji
Bioscience, Biotechnology and Biochemistry, 2002 , vol. 66, # 7 p. 1531 - 1537
反应条件
1: 1.) Mg / 1.) THF, 4 h, reflux, 2.) THF, -5 deg C, 16 h
2: 90 percent / PCC / CH2Cl2 / 24 h / Ambient temperature
3: 1.) HCl / 1.) CH3OH, 2.) pyridine, room temperature, 3 h
4: 90 percent / NaBr / dimethylformamide / 40 h / 45 °C
View Scheme
参考文献
Braconnier, M.F.; Braekman, J.C.; Daloze, D.
Bulletin des Societes Chimiques Belges, 1985 , vol. 94, # 8 p. 605 - 614
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
