Cyclopropanecarboxaldehyde → Cyclopropyl-(7-methoxybenzofuran-2-yl)-methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-methoxybenzofuran (2.0 g) in tetrahydrofuran (30 ml) cooled to -60° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (1.6M in hexanes, 8.9 ml). After stirring at -60° C. for 10 minutes, magnesium bromide diethyl etherate (3.8 g) was added in single portion and the reaction mixture stirred at -50° C. for 10 minutes. After cooling to -78° C., cyclopropane carboxaldehyde (1.0 ml) was added in a single portion and the mixture allowed to warm slowly to room temperature and stirred for 1 h. Water (2 ml) was added and the tetrahydrofuran removed in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml); the aqueous layer was extracted with ethyl acetate (50 ml); the organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 0-5% methanol in dichloromethane afforded the title compound as a yellow gum (1.88 g).

Provenance & Evidence