Hydrochloric Acid → HCID 11788723, compound

Participants

Reaction Steps

To a 0° C. solution of 4-methoxyphenylmagnesium bromide (1M in THF) (30 ml, 30.0 mmol) was added dropwise 3-ethoxycyclopent-2-en-1-one (3.56 ml, 30.0 mmol). The reaction mixture was stirred at RT overnight. 1M aqueous hydrochloric acid and EtOAc were added. There was emulsion. The biphasic mixture was filtered through a Celite® pad. Extracted filtrate three times with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The Celite®/filtered solids were stirred in EtOAc/combined aqueous layers. The solids were filtered, separated filtrate layers, and extracted aqueous once more with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The two crude product batches were combined and purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound. Mass spectrum (ESI) 189.3 (M+1).

Provenance & Evidence