Hydrochloric Acid → 2-(3,4-Dimethoxybenzoyl)furan

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Reaction Steps

Freshly distilled furan (57 ml, 790 mmoles) in dry ether (500 ml) is cooled (5° C) under nitrogen and n-butyllithium (340 ml, 2.35M in hexane) is added dropwise to the stirred solution. The mixture is stirred for 3 days at room temperature. The mixture is cooled to -30° C and a solution of 3,4-dimethoxybenzonitrile (77.5 g, 480 mmoles, described in Example I) in ether (200 ml) is added dropwise to the mixture. The brown mixture is stirred for 5 hours at room temperature. Wet tetrahydrofuran is cautiously added and the mixture is poured on ice. Hydrochloric acid (3N) is added until the mixture is acidic. The mixture is extracted with ether. The aqueous phase is rendered basic and extracted with methylene chloride. The organic extract is washed with brine, dried and evaporated. The residue is subjected to chromatography on silica gel using chloroform and the eluates are evaporated to give the title compound, mp 112°-114° C.

Provenance & Evidence