Ethyl chloroformate → Diethyl 2-(4-(benzyloxy)phenyl)malonate

Participants

Reaction Steps

A heptane solution of LDA (2.0 M, 36.4 ml, 72.8 mmols) was dropwise added to a THF (130 ml) solution of ethyl 4-benzyloxyphenylacetate (13.1 g, 48.5 mmols) and ethyl chlorocarbonate (9.25 ml, 97.0 mmols), under a nitrogen stream at −70° C. or lower. The reaction mixture was stirred for 15 minutes, then a saturated aqueous ammonium chloride solution was added thereto, and the resulting mixture was allowed to warm to room temperature, and then extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting residue was washed with hexane to obtain the entitled compound (13.8 g) as crystals, which were further recrystallized from hexane.

Provenance & Evidence