2-(4-戊炔氧基)四氢-2H-吡喃合成路线 （共 70 条）
反应条件
1: 84 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide 2: LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 140 °C 3: p-toluenesulfonic acid / H2O; methanol View Scheme
参考文献
Griepink, Frans C.; Van Beek, Teris A.; Posthumus, Maarten A.; De Groot, Aede; Visser, J. Hans; Voerman, Simon
Tetrahedron Letters, 1996 , vol. 37, # 3 p. 411 - 414
反应条件
1: 84 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide 2: H2 / P-2 Ni / ethanol 3: p-toluenesulfonic acid / H2O; methanol View Scheme
参考文献
Griepink, Frans C.; Van Beek, Teris A.; Posthumus, Maarten A.; De Groot, Aede; Visser, J. Hans; Voerman, Simon
Tetrahedron Letters, 1996 , vol. 37, # 3 p. 411 - 414
反应条件
1: 1.) n-BuLi, 2.) HMPA / 1.) THF, 0 deg C, 30 min, 2.) THF, a) 0 deg C, 30 min, b) RT, 6 h 2: p-toluenesulfonic acid, H2O / methanol / Ambient temperature View Scheme
参考文献
Trost; Shi
Journal of the American Chemical Society, 1993 , vol. 115, # 26 p. 12491 - 12509
反应条件
1: 1-(tetrahydropyran-2-yloxy)-4-pentyne With ammonia; lithium; iron nitrate (III) in diethyl ether T=-70°C; 1 h; Inert atmosphere; 2: oxirane in diethyl ether Inert atmosphere;
参考文献
Subba Reddy; Borkar, Prashant; Yadav; Purushotham Reddy; Kunwar; Sridhar; Gree, Rene
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 7 p. 1349 - 1358
反应条件
n-butyllithium; benzophenone; CaH2; sodium in tetrahydrofuran; hexane
参考文献
G. D. Searle and Co.
Patent: US4952710 A1, 1990 ;
反应条件
1: 1-(tetrahydropyran-2-yloxy)-4-pentyne With n-butyllithium in tetrahydrofuran; hexane T=0°C; 0.25 h; 2: With N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane T=0°C; 0.25 h; 3: tridecyl iodide in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane 20 h;
参考文献
Fletcher, Steven; Ahmad, Ayesha; Perouzel, Eric; Jorgensen, Michael R.; Miller, Andrew D.
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 196 - 199
反应条件
lithium in tetrahydrofuran; ammonia; dimethyl sulfoxide T=-60 - 20°C;
参考文献
Pisch, Sandra; Bornscheuer, Uwe T.; Meyer, Hartmut H.; Schmid, Rolf D.
Tetrahedron, 1997 , vol. 53, # 43 p. 14627 - 14634
反应条件
(i) Li, liq. NH3, (ii) /BRN= 1733136/; Multistep reaction;
参考文献
Bohlmann,F. et al.
Chemische Berichte, 1969 , vol. 102, p. 3283 - 3292
反应条件
1: 1.) sodium amide, 2.) hexamethylphosphoramide / 1.) THF, 50 deg C, 1.5 h, 2.) room temperature, 1 h 2: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 3: triethylamine / CH2Cl2 / 1 h / -5 °C 4: sodium iodide / acetone / 2 h / 50 °C 5: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 6: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 7: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme
参考文献
Shiraishi, Mitsuru; Terao, Shinji
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 8 p. 1591 - 1599
反应条件
1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 87 percent / tetrahydrofuran; hexane / 3.5 h / -78 - 20 °C 2.1: DIBALH / diethyl ether; hexane / 16 h / 20 °C 2.2: 78 percent / TsOH*H2O / methanol / 10 h / 20 °C 3.1: 0.3 percent / TsOH*H2O / CHCl3 / 10 h / 60 °C View Scheme
参考文献
Miura; Okajima; Hondo; Nakagawa; Takahashi; Hosomi
Journal of the American Chemical Society, 2000 , vol. 122, # 46 p. 11348 - 11357
