[6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methanol → [6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methane

Participants

Reaction Steps

A solution of 400 mg (1.02 mmol) of [6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methanol was dissolved in 10 mL of n-propylbenzene and 200 mg (5.25 mmol) of LiAlH4 was added. The reaction mixture was heated to reflux under a nitrogen atmoshere for 45 minutes. After sixteen hours, the reaction was quenched by the addition of 5 mL of water. To this suspension was added 3 mL of 15% (W/N) NaOH and an additional 3 mL of water. This suspension was filtered. The resulting filterate separated into two layers. The top (organic) layer was removed and evaporated to dryness. The crude product was chromatographed on silica eluted with 20% EtOAc in hexane. The final product was crystallized from ether. This yielded 100 mg of the title compound as a solid with a low melting point.

Provenance & Evidence