2-(4-戊炔氧基)四氢-2H-吡喃合成路线 （共 70 条）
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C
1.2: 97 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C
2.1: 65 percent / DIBALH / diethyl ether; hexane / 40 h / 20 °C
3.1: 92 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
4.1: 99 percent / NH2OH*HCl; Na2CO3 / H2O / 1 h / 20 °C
5.1: 84 percent / LAH / diethyl ether; diisopropyl ether / 24 h / 55 °C
6.1: 96 percent / Et3N / CH2Cl2 / 1 h
7.1: 93 percent / TiCl4 / CHCl3 / 3.3 h / 20 °C
8.1: 98 percent / TBAF; H2O2; KHCO3 / tetrahydrofuran; H2O; methanol / 6 h / 40 °C
View Scheme
参考文献
Miura, Katsukiyo; Hondo, Takeshi; Nakagawa, Takahiro; Takahashi, Tatsuyuki; Hosomi, Akira
Organic Letters, 2000 , vol. 2, # 3 p. 385 - 388
反应条件
1: 1-(tetrahydropyran-2-yloxy)-4-pentyne With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 2 h;
2: dimethyl (iodomethyl)-phenylsilane in tetrahydrofuran; hexane
16 h; Heating; Further stages.;
参考文献
Organ, Michael G.; Mallik, Debasis
Canadian Journal of Chemistry, 2006 , vol. 84, # 10 p. 1259 - 1262
反应条件
Yield given. Multistep reaction;
参考文献
Samsel; Norton
Journal of the American Chemical Society, 1984 , vol. 106, # 19 p. 5505 - 5512
反应条件
1: n-BuLi, HMPA / tetrahydrofuran / 3 h / 5 - 20 °C
2: p-Tos-OH / methanol / 10 h / Ambient temperature
View Scheme
参考文献
Carling, Robert W.; Clark, J. Stephen; Holmes, Andrew B.; Sartor, Dirk
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992 , # 1 p. 95 - 102
参考文献
Tomida, Ichiro; Iwakoshi, Kenji; Kono, Satoshi; Takahashi, Takeshi; Matsunaga, Taiki; Kayahara, Hiroshi
Agricultural and Biological Chemistry, 1987 , vol. 51, # 3 p. 939 - 940
反应条件
1: 1.) lithium amide / 1.) dimethoxyethane, reflux, 5 h, 2.) reflux, overnight
2: methanol, p-toluenesulfonic acid / 4 h / Heating
View Scheme
参考文献
Macaulay, Suzanne R.
Canadian Journal of Chemistry, 1980 , vol. 58, p. 2567 - 2572
反应条件
1.1: n-BuLi / tetrahydrofuran
1.2: tetrahydrofuran / 20 h / -60 - 60 °C
2.1: H2SO4 / methanol / 20 h / 20 °C
3.1: H2 / P-2 Ni / ethanol / 4 h / 20 °C
View Scheme
参考文献
Hiemstra, Henk; Sno, Michiel H. A. M.; Vijn, Robert J.; Speckamp, W. Nico
Journal of Organic Chemistry, 1985 , vol. 50, # 21 p. 4014 - 4020
反应条件
2: 95 percent / sodium bismethoxyethoxyaluminum hydride (Red-Al) / diethyl ether / 1.) 0 deg C, 1 h; 2.) room temp., 12 h
3: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 0 °C
View Scheme
参考文献
Marshall, James A.; Audia, James E.; Grote, Jonathan; Shearer, Barry G.
Tetrahedron, 1986 , vol. 42, # 11 p. 2893 - 2902
反应条件
1: n-butyllithium; N,N,N',N',N'',N''-hexamethylphosphoric triamide / tetrahydrofuran / -78 - 20 °C
2: Jone's reagent / acetone / 0 - 20 °C
3: hydrogen / ethanol / 20 °C
View Scheme
参考文献
Kai, Kenji; Kasamatsu, Koji; Hayashi, Hideo
Tetrahedron Letters, 2012 , vol. 53, # 40 p. 5441 - 5444
反应条件
2: 95 percent / sodium bismethoxyethoxyaluminum hydride (Red-Al) / diethyl ether / 1.) 0 deg C, 1 h; 2.) room temp., 12 h
3: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 0 °C
4: n-BuLi / tetrahydrofuran / 1 h / -78 °C
5: Dowex AG 50 W acidic ion exchange resin / methanol / 3 h / 40 °C
View Scheme
参考文献
Marshall, James A.; Audia, James E.; Grote, Jonathan; Shearer, Barry G.
Tetrahedron, 1986 , vol. 42, # 11 p. 2893 - 2902
