Water → (3-pyrrolidin-1-ylphenyl)methanol

Participants

Reaction Steps

0.25 g of N-(3-ethoxycarbonylphenyl)succinimide [synthesized by heat condensing ethyl m-aminobenzoate with succinic anhydride in acetic acid] was dissolved in 5 ml of anhydrous tetrahydrofuran, and with stirring under ice cooling, 0.17 g of lithium aluminium hydride was added. The mixture was maintained at room temperature for 30 minutes, and then heated under reflux for 4 hours. After the reaction, ethyl acetate and water were added. The organic layer was separated, and then worked up in a customary manner and purified by medium-pressure liquid chromatography [Lobar column, size B, Lichroprep Si 60 (E. Merck & Co.); eluting solvent: hexane/ethyl acetate=10/1) to give 84 mg (yield 47%) of the captioned compound as a colorless oil.

Provenance & Evidence