反应详情

温度

90 °C

A solution of 4-cyano-4-[3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.75 g, 2.4 mmol) and concentrated hydrochloric acid (2 mL) in methanol (10 mL) was heated at reflux under an argon atmosphere for 2 h. The mixture was cooled, was diluted with water and was extracted three times with methylene chloride. The organic extract was dried (magnesium sulfate) and was evaporated to the phenol (0.54 g, 92%). A vigorously stirred mixture of this phenol, 4-fluorobenzyl bromide (0.83 mL, 6.6 mmol) and potassium carbonate (0.92 g, 6.6 mmol) in dimethylformamide (12 mL) was heated under an argon atmosphere at 90° C. for 2 h. The mixture was allowed to cool, was diluted with water and was extracted three times with ether. The organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 30% ethyl acetate/hexanes, provided a white solid (0.6 g, 78%): m.p. 145°-146° C.

1. temperatureat reflux under an argon atmosphere for 2 h
2. temperatureThe mixture was cooled
3. extractionwas extracted three times with methylene chloride
4. extractionThe organic extract
5. dry with materialwas dried (magnesium sulfate)
6. customwas evaporated to the phenol (0.54 g, 92%)
7. temperatureto cool
8. extractionwas extracted three times with ether
9. extractionThe organic extract
10. dry with materialwas dried (magnesium sulfate)
11. customthe solvent was removed in vacuo
12. customPurification by flash chromatography
13. washeluting with 30% ethyl acetate/hexanes