2-[(7-溴庚基)氧基]四氢-2H-吡喃合成路线 （共 23 条）
反应条件
hydrogenchloride T=20°C; 16 h;
参考文献
Donde, Yariv
Patent: US2009/124676 A1, 2009 ;
Location in patent: Page/Page column 5 ;
US 20090124676 A1
反应条件
1: 75 percent / aq. HBr / 40 h / 80 °C 2: 100 percent / aq. HCl / 16 h / 20 °C View Scheme
参考文献
Mozuraitis, Raimondas; Buda, Vincas; Liblikas, Ilme; Unelius, Carl Rikard; Borg-Karlson, Anna-Karin
Journal of chemical ecology, 2002 , vol. 28, # 6 p. 1191 - 1208
反应条件
1: NaBH4 / tetrahydrofuran; H2O / 70 h / Ambient temperature 2: pyridine / 4 °C 3: 1.) 2,6-dimethylpyridine; 2.) H2/Pd/C / 1.) 170 deg C, 4 h; 2.) AcOH, 60 deg C, 1 h View Scheme
参考文献
Uesato, Shinici; Takeda, Yoshio; Hashimoto, Toshihiro; Uobe, Kenichi; Inouye, Hiroyuki; et al.
Helvetica Chimica Acta, 1984 , vol. 67, p. 2111 - 2127
反应条件
carbon tetrabromide; triphenylphosphine
参考文献
Smallheer, Joanne M.; McHugh, Robert J.; Chang, Chong-Hwan; Kaltenbach III, Robert F.; Worley, Tabitha V.; Klabe, Ronald M.; Bacheler, Lee T.; Rayner, Marlene M.; Erickson-Viitanen, Susan; Seitz, Steven P.
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 11 p. 1365 - 1370
反应条件
2: CBr3, PPh3 View Scheme
参考文献
Smallheer, Joanne M.; McHugh, Robert J.; Chang, Chong-Hwan; Kaltenbach III, Robert F.; Worley, Tabitha V.; Klabe, Ronald M.; Bacheler, Lee T.; Rayner, Marlene M.; Erickson-Viitanen, Susan; Seitz, Steven P.
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 11 p. 1365 - 1370
反应条件
2: CBr3, PPh3 View Scheme
参考文献
Smallheer, Joanne M.; McHugh, Robert J.; Chang, Chong-Hwan; Kaltenbach III, Robert F.; Worley, Tabitha V.; Klabe, Ronald M.; Bacheler, Lee T.; Rayner, Marlene M.; Erickson-Viitanen, Susan; Seitz, Steven P.
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 11 p. 1365 - 1370
反应条件
1: 94 percent 2: 1) EtMgBr, CuI 3: TsOH / methanol; H2O 4: 89 percent / PCC View Scheme
参考文献
Ishmuratov; Ishmuratova; Odinokov; Tolstikov
Chemistry of Natural Compounds, 1997 , vol. 33, # 1 p. 25 - 30
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 1.2: -20 - 20 °C 2.1: Jone's reagent / acetone / 0 - 4 °C View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
1: 1.) Mg, 2.) CuI / 1.) THF, 1 h, 2.) 0 deg C, 80 min 2: aq. HOAc / tetrahydrofuran / 1.5 h 3: 60 percent / pyridine / tetrahydrofuran / 1.) -30 deg C, 1 h, 2.) 0 deg C, 16 h 4: LiBr / acetone / 2 h / Heating 5: tetrahydrofuran / Heating 6: LDA / tetrahydrofuran / -78 °C 7: Li(sec-Bu)3BH / tetrahydrofuran / -10 °C 8: hexamethylphosphoric acid triamide / 1 h / 110 °C 9: Bu3SnH, AIBN / toluene / 1 h / 60 °C View Scheme
参考文献
Neeland, Edward G.; Ounsworth, James P.; Sims, Russel J.; Weiler, Larry
Journal of Organic Chemistry, 1994 , vol. 59, # 24 p. 7383 - 7394
反应条件
1: 1.) BuLi, HMPA / 1.) THF, -30 deg C, 2.) THF, from -30 deg C to RT 2: 90.3 percent / 10 percent HCl / methanol / 2 h / Heating 3: 87.7 percent / SOCl2, pyridine / benzene / 50 °C 4: 91.6 percent / NaI / butan-2-one / 14 h / Heating 5: 1.) BuLi, HMPA / 1.) THF, 0 deg C, 2.) THF, 0 deg C, 1 h, then RT 6: 91.7 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 7: Fe2(CO)9, H2O / benzene / 0.5 h / 45 °C 9: 83.1 percent / H2 / Pd/CaCO3 / hexane / 16 h / Ambient temperature 10: 82 percent / 10 percent NaOH / ethanol / 2 h / Heating View Scheme
参考文献
Satoh, Mitsuru; Takeuchi, Naoki; Fujita, Takeshi; Yamazaki, Katsuya; Tobinaga, Seisho
Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 10 p. 1501 - 1505
