Water → phenylacetic anhydride

Participants

Reaction Steps

A 1.50 M sodium hydroxide solution was added to the hydrochloride salt of (S)-2-amino-2-cyclohexyl-3-butyne 30 (1 equiv). A solution of anhydride (0.17 M, 1 equiv) in chloroform was added to the above solution and heated at reflux for 24 h. The reaction mixture was transferred to a reparatory funnel, and EtOAc (150 mL) and water (15 mL) were added. The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (1:1 hexanes:EtOAc) to afford the desired product.

Provenance & Evidence