Phenol → HCID 58885445, compound

Participants

Reaction Steps

A solution of 2-chloro-3-oxo-pentanoic acid methyl ester (20 g, 121.5 mmol) in acetone (100 ml) was added to the phenol from Preparation 3 (17.5 g, 121.5 mmol) and caesium carbonate (43.5 g, 133.6 mmol) in acetone (400 ml) under a nitrogen atmosphere. The mixture was stirred at room temperature for 15 minutes and then heated under reflux for 2.5 hours. Water was added and the solvent was evaporated under reduced pressure. The residual aqueous solution was extracted with dichloromethane (3×300 ml) and the combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residual orange oil was pre-adsorbed onto silica gel and then purified by chromatography on silica gel using ethyl acetate in pentane (gradient from 20:80 to 80:20) to give the title compound as a yellow solid (27 g).

Provenance & Evidence