反应详情

温度

0 °C

Dissolved 55 uL 4-fluoroaniline in 1.3 mL CH2Cl2 then cooled to 0° C. and added 0.21 mL AlMe3 (2.0M in toluene). Warmed to RT, stirred for 30 minutes, then added 50 mg (1aS,4aR,8aS)-hexahydro-1aH,6H-oxireno[e]chromene (7-5) in 1.0 mL CH2Cl2. Stirred for two hours at RT, then sat. sodium potassium tartrate solution was added dropwise to the reaction, allowing gas evolution to cease between drops, until no further gas evolution was noted. The mixture was diluted with water, then extracted with CH2Cl2. The extract was dried over Na2SO4, filtered, concentrated, then purified on silica (0-40% EtOAc in hexanes) to yield the title compound. 1H NMR (500 MHz, CDCl3) δ=1.42-1.69 (m, 7H), 1.90-2.09 (m, 3H), 2.47 (s, 1H), 3.38-3.48 (m, 3H), 3.53 (s, broad, 1H), 3.92-3.95 (m, 1H), 6.54-6.59 (m, 2H), 6.84-7.26 (m, 2H) ppm. HRMS (ES) m/z M±H calc'd: 266.1551. found 266.1551.

1. temperatureWarmed to RT
2. stirringStirred for two hours at RT
3. extractionextracted with CH2Cl2
4. dry with materialThe extract was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. custompurified on silica (0-40% EtOAc in hexanes)