ethyl 4-phenylmethoxybutanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a stream of argon, 248 ml of tetrahydrofuran was added to 26 g (0.65 mole) of 60% sodium hydride, and a solution of 72.2 g (0.325 moles) of ethyl 4-benzyloxybutyrate and 26.7 g (0.65 mole) of acetonitrile in 94 ml of anhydrous tetrahydrofuran was added dropwise over the course of 40 minutes, and the mixture was heated under reflux for 2.5 hours. After cooling, the reaction mixture was poured into ice water, and washed with a 1:1 mixture of hexane and ether. The aqueous layer was acidified with concentrated hydrochloric acid, and extracted with ether. The ether layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting crude 6-benzyloxy-3-ketohexanenitrile was subjected to silica gel column chromatography. The column was eluted with a 1:1 mixture of hexane and ether to give 57.8 g (81.2%) of a pale yellow oily product. the mixture was heated under reflux for 2.5 hours After cooling washed with a 1:1 mixture of hexane and ether extracted with ether The ether layer was washed with water a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure The column was eluted with a 1:1 mixture of hexane and ether