(6-溴-1,3-苯并二氧代l-5-基)甲醇合成路线 （共 37 条）
反应条件
1: SOCl2 2: 76 percent / NaH / dimethylformamide; tetrahydrofuran / 5 h / 80 °C 3: 27 percent / P2O5; POCl3 / 2 h / Heating 4: 99 percent / Rose Bengal; O2 / methanol; CH2Cl2 / 0.33 h / 18 °C / UV-irradiation 5: 99 percent / LiAlH4 / tetrahydrofuran / 15 h / Heating 6: 78 percent / NaOAc; pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Wada, Yasuhiro; Kaga, Harumi; Uchiito, Shiho; Kumazawa, Eri; Tomiki, Miho; Onozaki, Yu; Kurono, Nobuhito; Tokuda, Masao; Ohkuma, Takeshi; Orito, Kazuhiko
Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7301 - 7306
反应条件
sodium hydride 1) THF, room temp., 1 h; 2) room temp.; Yield given. Multistep reaction;
参考文献
Khanapure, Subhash P.; Biehl, Edward R.
Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1471 - 1475
反应条件
2,2,6,6-tetramethyl-piperidine-N-oxyl; iron(III) chloride in water; ethyl acetate 3 h; Heating;
参考文献
Kumar, R. Senthil; Karthikeyan; Perumal, Paramasivan T.
Canadian Journal of Chemistry, 2008 , vol. 86, # 7 p. 720 - 725
反应条件
1: 1) n-BuLi / 1) ether, hexane, -78 deg C, 5 min, 2) a) to 23 deg C, 2 h, b) 23 deg C, 8 h
2: 89 percent / imidazole / tetrahydrofuran / 8 h / 23 °C
3: 74 percent / LiClO4 / diethyl ether / 24 h / 23 °C
4: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
5: Et3N / CH2Cl2 / 1 h / -50 °C
6: Bu4NN3 / tetrahydrofuran / 2 h
7: Bu4NN3 / tetrahydrofuran / 9 h
View Scheme
参考文献
Pearson; Schkeryantz
Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6783 - 6789
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 1 h
1.2: 81 percent / tetrahydrofuran; hexane / 0.67 h / -78 °C
2.1: 61 percent / pyridinium chlorochromate; Al2O3 / CH2Cl2 / 2 h / 20 °C
3.1: 60 percent / LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 20 °C
4.1: 83 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 - 0 °C
5.1: 71 percent / BaMnO4 / CH2Cl2 / 16 h / 20 °C
View Scheme
参考文献
Flanagan, Stuart R; Harrowven, David C; Bradley, Mark
Tetrahedron, 2002 , vol. 58, # 30 p. 5989 - 6001
反应条件
Grignard Reaction; Schlenk techniqueInert atmosphere;
参考文献
Reddy, A. Gopi Krishna; Krishna; Satyanarayana
Tetrahedron, 2013 , vol. 69, # 47 p. 10098 - 10107
反应条件
sodium hydride
1.) DMF, 0 deg C, 2.) rt, 3 h; Yield given. Multistep reaction;
参考文献
Paleo, M. Rita; Lamas, Carlos; Castedo, Luis; Dominguez, Domingo
Journal of Organic Chemistry, 1992 , vol. 57, # 7 p. 2029 - 2033
参考文献
Mann, John; Piper, Susan E.
Journal of the Chemical Society, Chemical Communications, 1982 , # 8 p. 430 - 432
反应条件
bis(1,5-cyclooctadiene)nickel (0) in N,N-dimethyl-formamide
参考文献
Semmelhack, M.F.; Helquist, Paul; Jones, L.D.; Keller, Leonard; Mendelson L.; et al.
Journal of the American Chemical Society, 1981 , vol. 103, # 21 p. 6460 - 6471
反应条件
1: 4-bromo-5-hydroxymethyl-1,2-methylenedioxybenzene With n-butyllithium in tetrahydrofuran
T=-78°C; 0.5 h;
2: carbon dioxide in tetrahydrofuran; diethyl ether
0.5 h;
3: With hydrogenchloride in tetrahydrofuran; diethyl ether; water
16 h;
参考文献
Beck, Daniel E.; Agama, Keli; Marchand, Christophe; Chergui, Adel; Pommier, Yves; Cushman, Mark
Journal of Medicinal Chemistry, 2014 , vol. 57, # 4 p. 1495 - 1512
