Water → HCID 68871013, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-acetamidophenol (10.8 g, 72 mmol) in DMF (50 mL) was added dropwise to a slurry of NaH (60% in oil, 2.88 g, 72 mmol) over 1 h. A solution of the product from Step 1 (13.7 g, 36.0 mmol) in DMF (50 mL) was added and the resulting mixture was heated to 60° C. overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to give an oil which was purified by chromatography (10-100% EtOAc in hexanes) to give the title compound (4.6 g, 34%) as an orange solid. MS (ES+) m/e 381 [M+H]+.

Provenance & Evidence