反应详情

A mixture containing 45 g of ethyl 4-chlorobenzoate in 235 ml of anhydrous THF and 19.50 g of NaH (60% in mineral oil) in 235 ml of anhydrous TBF is placed under nitrogen. 36 ml of acetone and 750 ml of additional anhydrous THF are added dropwise at 0° C., and it is heated under reflux for 3 hours. The mixture is acidified to pH=5 by addition of 2N HCl then it is extracted with ether and washed with water and then with saturated NaHCO3 solution; it is dried over MgSO4 and concentrated. The raw product is dissolved in a minimum of toluene, the insoluble matter is filtered then it is purified by chromatography on silica, eluting with cyclohexane/AcOEt mixture (95/5; v/v). 47.9 g of the expected compound is obtained.

1. temperatureit is heated
2. temperatureunder reflux for 3 hours
3. extractionit is extracted with ether
4. washwashed with water
5. dry with materialit is dried over MgSO4
6. concentrationconcentrated
7. dissolutionThe raw product is dissolved in a minimum of toluene
8. filtrationthe insoluble matter is filtered
9. customit is purified by chromatography on silica
10. washeluting with cyclohexane/AcOEt mixture (95/5; v/v)