Tetrahydrofuran → [1-(1-Hydroxypropan-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

Participants

Reaction Steps

In 10 ml of methanol was dissolved 1.24 g (4.15 mmoles) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)-2-methylethyl acetate. Tetrahydrofuran (30 ml) and then 10 ml (10.0 mmoles) of an 1.0 N aqueous solution of sodium hydroxide was added. The mixture was stirred for 3 hours at room temperature. The solvent was distilled off under reduced pressure. The residue was extracted with 50 ml of ethyl acetate three times, and the resulting extracts were dried over anhydrous magnesium sulfate, and concentrated to afford 900 mg of a crude product. The crude product was chromatographed on a column of silica gel using cyclohexane/ethyl acetate (1/1) as an eluent to afford compound (106) (790 mg, 3.07 mmoles, 74.1%).

Provenance & Evidence