Hydrochloric Acid → HCID 69758873, compound

Participants

Reaction Steps

Phenylacetyl chloride was slowly added dropwise into a mixture of 110 g of Meldrum's acid, 120 ml of pyridine and 500 ml of dichloromethane under stirring in an ice bath. After stirring overnight as it was, 650 ml of an aqueous 1.2 N hydrochloric acid solution was added to the mixture. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. To the residue was added 600 ml of tert-butanol, followed by heating under reflux for 3 hours. After cooling as it was, the solvent was removed while ethanol was added. To the residue were added 600 ml of toluene and 110 ml of N,N-dimethylformamidodimethylacetal, followed by heating under stirring for 2 hours in an oil bath kept at 100° C. while removing methanol by using Dean-Stark apparatus. The reaction solution was evaporated, and the residue was subjected to silica gel column chromatography using 50-70% ethyl acetate/hexane, to give 93 g of the target compound.

Provenance & Evidence