5-溴-2-甲基-2-戊烯合成路线 （共 93 条）
反应条件
1: (i) Mg, (ii) /BRN= 102378/
2: tetrahydrofuran
3: HCO2Na, HCO2H
View Scheme
参考文献
Johnson,W.S.; Owyang,R.
Journal of the American Chemical Society, 1964 , vol. 86, p. 5593 - 5598
反应条件
1: 79 percent / n-butyl lithium, HMPA / hexane; tetrahydrofuran / 0.08 h / -78 °C
2: alkaline hydrogen peroxide
View Scheme
参考文献
Amupitan, Joseph A.; Huq, Enamul; Mellor, Michael; Scovell, Edward G.; Sutherland, James K.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 4 p. 747 - 749
反应条件
2: 1.) 1.6M n-BuLi / 1.) ether, -70 deg C, 20 min, 2.) -70 deg C, 30 min; up to room temp.
View Scheme
参考文献
Parr, William J. E.
Journal of Chemical Research, Miniprint, 1981 , # 11 p. 4101 - 4130
反应条件
2: 94 percent / lithium aluminum hydride / diethyl ether / 1.) from -77 deg C to -60 deg C, 2.) -45 deg C, 15 min
3: 96 percent / pyridine / 1.) 0 deg C, 30 min, 2.) RT, 20 h
4: 62 percent / pyridinium p-toluenesulfonate (PPTS) / ethanol / 4 h / 55 °C
5: 55 percent / (Et2N)(Me2N)SF2 / CCl3F / 1.) -70 deg C, 45 min, 2.) RT, 1 h
6: 83 percent / potassium carbonate / methanol / 0.17 h / Ambient temperature
View Scheme
参考文献
Poulter, C. Dale; Wiggins, Paul L.; Plummer, Thomas L.
Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1532 - 1538
反应条件
2: 94 percent / lithium aluminum hydride / diethyl ether / 1.) from -77 deg C to -60 deg C, 2.) -45 deg C, 15 min
3: 96 percent / pyridine / 1.) 0 deg C, 30 min, 2.) RT, 20 h
4: 62 percent / pyridinium p-toluenesulfonate (PPTS) / ethanol / 4 h / 55 °C
View Scheme
参考文献
Poulter, C. Dale; Wiggins, Paul L.; Plummer, Thomas L.
Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1532 - 1538
反应条件
1: 1.) Mg / 1.) ether; 2.) ether, 0.5 h
2: 18 percent / phosphorus oxychloride, pyridine / 2.33 h
View Scheme
参考文献
Poulter, C. Dale; Wiggins, Paul L.; Plummer, Thomas L.
Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1532 - 1538
反应条件
2: 94 percent / lithium aluminum hydride / diethyl ether / 1.) from -77 deg C to -60 deg C, 2.) -45 deg C, 15 min
3: 96 percent / pyridine / 1.) 0 deg C, 30 min, 2.) RT, 20 h
4: 62 percent / pyridinium p-toluenesulfonate (PPTS) / ethanol / 4 h / 55 °C
5: 55 percent / (Et2N)(Me2N)SF2 / CCl3F / 1.) -70 deg C, 45 min, 2.) RT, 1 h
View Scheme
参考文献
Poulter, C. Dale; Wiggins, Paul L.; Plummer, Thomas L.
Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1532 - 1538
反应条件
1: (i) Mg, (ii) /BRN= 102378/
2: tetrahydrofuran
3: HCO2Na, HCO2H
View Scheme
参考文献
Johnson,W.S.; Owyang,R.
Journal of the American Chemical Society, 1964 , vol. 86, p. 5593 - 5598
反应条件
1.1: 92 percent / NaI / acetone / 20 h / 20 °C
2.1: t-BuLi / diethyl ether / 1 h / -78 °C
2.2: 52 percent / diethyl ether / 4 h / -78 °C
3.1: aq. KOH / ethanol / 20 h / Heating
4.1: aq. HCl / 100 °C / 0.4 Torr
View Scheme
参考文献
Hiranuma; Hudlicky
Tetrahedron Letters, 1982 , vol. 23, # 34 p. 3431 - 3434
反应条件
magnesium in tetrahydrofuran; diethyl ether
T=-78°C; 5 h;
参考文献
Blanc, Aurelien; Toste, F. Dean
Angewandte Chemie - International Edition, 2006 , vol. 45, # 13 p. 2096 - 2099
