Methyl 2-(1H-pyrrol-1-yl)benzoate → (2-(1H-pyrrol-1-yl)phenyl)methanol

Participants

Reaction Steps

To a suspension of 117 g of lithium aluminum hydride in 2 L of anhydous ether (under an inert atmosphere) is added dropwise a solution of 428 g of methyl 2-(pyrrol-1-yl)-benzoate in 1.5 L of ether over a period of 4 hours. The reaction mixture is then heated at reflux temperature for an additional 4 hours and then allowed to cool to room temperature. After cooling in an ice-bath, the excess lithium aluminum hydride is destroyed by the dropwise addition of 117 ml of water over 1 hour, followed by dropwise addition of 117 ml of 15% sodium hydroxide and subsequent addition of 351 ml of water over a 30 minute period. The resultant granular solid is separated by filtration, the ether layer is then dried over magnesium sulfate and the solvent evaporated under reduced pressure to yield 2-(pyrrol-1-yl)-benzyl alcohol which may be further purified by distillation in vacuo; b.p. 110°-114°/0.1 mm Hg.

Provenance & Evidence