Diethyl Carbonate → HCID 23333808, compound

Participants

Reaction Steps

To a solution of 1.4 g (0.06 mole) of metallic sodium in 50 ml of ethanol was added 10 g (0.038 mole) of ethyl 4-(3-methyl-2-thienyl)phenylacetate [I.R. (liquid film): νC=O 1735 cm-1 ], followed by adding 14.3 g (0.121 mole) of diethyl carbonate. The mixture was stirred at 50° to 60° C. for 30 minutes and freed from the ethanol by distillation under reduced pressure. To the residue were added 15 ml of 1 N hydrochloric acid and 50 ml of benzene and the mixture was shaken thoroughly. The organic layer was dried over anhydrous magnesium sulfate and freed from the solvent by distillation under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: benzene/n-hexane=2/1) to obtain 7.8 g (58% yield) of oily diethyl [4-(3-methyl-2-thienyl)phenyl]malonate.

Provenance & Evidence