2-(6-溴己氧基)四氢-2H-吡喃合成路线 （共 75 条）
反应条件
1.1: triphenylphosphine / toluene / 1 h / 120 °C / |Inert atmosphere 1.2: 1 h / 20 °C / |Inert atmosphere 1.3: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / methanol / 2 h / 20 °C / |Inert atmosphere 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme
参考文献
Chang, Jun; Zhang, Si-Ji; Jiang, Yong-Wei; Xu, Liang; Yu, Jian-Ming; Zhou, Wen-Jiang; Sun, Xun
ChemMedChem, 2013 , vol. 8, # 6 p. 976 - 984
反应条件
1: KO-tBu, n-BuLi / hexane; diethyl ether / -78 deg C up to RT for 17 h 2: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h 3: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 4: 77 percent / HOAc / 6 h / 60 °C View Scheme
参考文献
Chan, T. H.; Koumaglo, K.
Journal of Organometallic Chemistry, 1985 , vol. 285, p. 109 - 120
反应条件
1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 3,5 h, 2.) THF, hexane, -10 deg C, 4 h 2: 87 percent / Raney nickel / 5 h / Heating 3: p-toluenesulfonic acid / methanol / 8 h / Ambient temperature View Scheme
参考文献
Deshmukh; Veeresh
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996 , vol. 35, # 12 p. 1239 - 1241
反应条件
1.1: Mg / tetrahydrofuran 1.2: 58 percent / Li2CuCl4 / tetrahydrofuran 2.1: 91 percent / Ph3P; 2,4,4,6-tetrabromocyclohexa-2,5-dienone / CH2Cl2 / 20 °C View Scheme
参考文献
Mohr, Wolfgang; Horn, Clemens R.; Stahl, Juergen; Gladysz
Synthesis, 2003 , # 8 p. 1279 - 1285
反应条件
1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.25 h 1.2: MnCl2 / tetrahydrofuran / 12 h / 20 °C 1.3: 70 percent / CuCl2; LiCl / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 6 h / 20 °C 2.1: 78 percent / TFA / methanol / 20 °C View Scheme
参考文献
Belmar, Julio; Tellez; Baeza; Freer
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 7 p. 583 - 586
反应条件
1: 58 percent / Li2CuCl4 / tetrahydrofuran / 4 h / -78 °C 2: 60.25 percent / PCC / CH2Cl2 / 1 h View Scheme
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
1: 6-[(Tetrahydropyran-2-yl)oxy]-1bromohexane With magnesium in tetrahydrofuran T=20°C; 2: With dilithium tetrachlorocuprate in tetrahydrofuran T=-78°C; 3: 12-(p-iodophenyl)dodecyl tosylate in tetrahydrofuran T=-78 - 20°C; 15 h;
参考文献
Pinchuk, Anatoly N.; Rampy, Mark A.; Longino, Marc A.; Skinner, R. W. Scott; Gross, Milton D.; Weichert, Jamey P.; Counsell, Raymond E.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 7 p. 2155 - 2165
反应条件
1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.25 h 1.2: MnCl2 / tetrahydrofuran / 12 h / 20 °C 1.3: 70 percent / CuCl2; LiCl / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 6 h / 20 °C 2.1: 78 percent / TFA / methanol / 20 °C 3.1: 94 percent / pyridine; DMAP / 12 h / 20 °C View Scheme
参考文献
Belmar, Julio; Tellez; Baeza; Freer
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 7 p. 583 - 586
反应条件
dimethylsulfide; triethylamine 1.) CH2Cl2, -50 deg C, 30 min 2.) -50 deg C, 1h; Yield given. Multistep reaction;
参考文献
Kim; Kee
Tetrahedron Letters, 1990 , vol. 31, # 20 p. 2899 - 2900
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 4: 80 percent / pyridine / 1 h / Heating View Scheme
参考文献
Canevet; Roeder; Vostrowsky; Bestmann
Chemische Berichte, 1980 , vol. 113, # 3 p. 1115 - 1120
