2-(4-戊炔氧基)四氢-2H-吡喃合成路线 （共 70 条）
反应条件
1: sodium amide; liquid ammonia
2: phosphoryl chloride
View Scheme
参考文献
Eglinton et al.
Journal of the Chemical Society, 1952 , p. 2873,2880
反应条件
Yield given. Multistep reaction;
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
反应条件
1: BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / -78 - 20 °C
2: 1.20 g / TsOH*H2O / methanol / 1 h / 20 °C
3: 58 percent / H2; quinoline / Pd/BaSO4 / methanol / 48 h / 20 °C / 760.05 Torr
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
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 °C / Inert atmosphere
1.2: 3 h / 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / ethanol / 3 h / 20 °C / Inert atmosphere
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -70 - -35 °C
3.2: 0.5 h / -35 - -5 °C
4.1: tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -70 - -35 °C
5.2: 0.5 h / -35 - -5 °C
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 - 90 °C / Inert atmosphere
7.1: water; sodium hydroxide / methanol / 1 h / 20 °C
View Scheme
参考文献
Kambe, Tohru; Maruyama, Toru; Nakano, Masayuki; Yamaura, Yoshiyuki; Shono, Tomoyuki; Seki, Akiteru; Sakata, Kiyoto; Maruyama, Takayuki; Nakai, Hisao; Toda, Masaaki
Chemical and Pharmaceutical Bulletin, 2011 , vol. 59, # 12 p. 1523 - 1534
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
View Scheme
参考文献
Tietze; Wunsch; Noltemeyer
Tetrahedron, 1992 , vol. 48, # 11 p. 2081 - 2099
反应条件
n-butyllithium; sulfuric acid
Yield given. Multistep reaction;
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
1.1: ethylmagnesium bromide / tetrahydrofuran / 50 °C
1.2: 20 - 50 °C
2.1: potassium tert-butylate; dimethyl sulfoxide / tetrahydrofuran / -40 °C
3.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
4.2: -78 - 20 °C
5.1: sodium hydride / diethyl ether; mineral oil / 0 °C
5.2: 0 °C
6.1: diisobutylaluminium hydride / diethyl ether / 0 °C
7.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
8.2: -78 - 20 °C
9.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
9.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1: 1.) sodium amide / 1.) Et2O, liquid NH3, -50 deg C to -40 deg C, 60 min., 2.) -50 deg C to -40 deg C, 100 min.
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 / pyridine-2,6-dicarboxylic acid, cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 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.) 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
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: 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: 5 percent / TiCl4 / CHCl3 / 3.3 h / 20 °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
