反应详情

Methyl p-[(diethoxyphosphoryl)methyl]benzoate (4.00 g, 13.97 mmoles, prepared as in Liebigs Ann. Chem. 1985, 929) was added to a 1M dimsyl anion solution in dimethylsulfoxide (12.71 mL,12.71 mmoles, prepared by warming sodium hydride in dimethylsulfoxide for 1 hour at 65° C.). After 30 minutes, the mixture was added to a solution of 1-(8-phenyl-2-naphthyl)ethanone (XIVa) (0.540 g, 2.19 mmoles) in dimethylsulfoxide (10.0 mL) at room temperature. After 2 hours at room temperature, a 1M solution of sodium ethoxide in ethanol (1.31 mL, 2.63 mmoles) was added. After 2 hours at room temperature, the mixture was diluted with saturated sodium bicarbonate (100 mL) and extracted with diethyl ether (100 mL×3). The solution was evaporated and the residue chromatographed (eluted with 5% ethyl acetate in hexane) over silica to give 0.500 g (yield: 64%) of 4-[2-(8-phenyl-2-naphthalenyl)-propenyl]benzoic acid, ethyl ester as a white solid. NMR indicated the ratio of E to Z isomers as 2:1.

1. waitAfter 2 hours at room temperature
2. waitAfter 2 hours at room temperature
3. extractionextracted with diethyl ether (100 mL×3)
4. customThe solution was evaporated
5. customthe residue chromatographed
6. wash(eluted with 5% ethyl acetate in hexane) over silica