2-(6-溴己氧基)四氢-2H-吡喃合成路线 （共 75 条）
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C
1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C
2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C
View Scheme
参考文献
Subchev; Harizanov; Francke; Franke; Plass; Reckziegel; Schroeder; Pickett; Wadhams; Woodcock
Journal of Chemical Ecology, 1998 , vol. 24, # 7 p. 1141 - 1151
反应条件
1: 65 percent / dimethylsulfoxide / 2 h / Ambient temperature
2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -78 deg C to RT, 1 h, 2.) THF, hexane, form -78 deg C to RT, 4 h
3: 68 percent / methanolic para-toluenesulfonic acid / toluene / 144 h
4: 88 percent / H2 / 10percent Pd/C / diethyl ether / 16 h
5: 44 percent / molecular sieves 4 A, pyridinum dichromate / dimethylformamide / 120 h / Ambient temperature
6: 94 percent / 10percent aq. tetrabutylammonium hydroxide / CH2Cl2 / 16 h
View Scheme
参考文献
Wallace, Paul A.; Minnikin, David E.; McCrudden, Katharine; Pizzarello, Andrea
Chemistry and Physics of Lipids, 1994 , vol. 71, # 2 p. 145 - 162
反应条件
1: 85 percent / lithium amide / liquid ammonia; tetrahydrofuran
2: 72 percent / Na; ammonia / diethyl ether
3: 91 percent / hydrogen chloride / methanol / 4 °C
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: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C
1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C
2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C
3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C
4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C
View Scheme
参考文献
Nakamura, Tsuyoshi; Watanabe, Yukiko; Shiozaki, Masao; Kanai, Saori; Kurakata, Shin-ichi
Bulletin of the Chemical Society of Japan, 2003 , vol. 76, # 5 p. 1011 - 1022
反应条件
NiCl2((PPh3)P)2; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine in tetrahydrofuran; hexane
Ambient temperature;
参考文献
Jeropoulos, Sotiris; Smith, Edward H.
Journal of the Chemical Society, Chemical Communications, 1986 , # 21 p. 1621 - 1622
反应条件
sodium iodide in acetone
Iodination; 20 h; Heating;
参考文献
Jones, Brian P.; Schildknegt, Klaas; Wright, Kathyrn F.; Showell, Henry J.; Dittami, James P.; McCarthy, Keith E.; Reiter, Lawrence A.
Heterocycles, 2000 , vol. 53, # 8 p. 1713 - 1724
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
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.) 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
5: 92 percent / H+
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
iodine; magnesium; ethylene dibromide
1.) 2-methyltetrahydrofuran, 45 min, 2.) - 15 deg C - room temperature, 120 min; Yield given. Multistep reaction. Yields of byproduct given;
参考文献
Poppe; Recseg; Novak
Synthetic Communications, 1995 , vol. 25, # 24 p. 3993 - 4000
