Methanol → 2-Methoxythiophene

Participants

Reaction Steps

2-Methoxythiophene was prepared by the procedures described in H. A. Keeystra et al., Tetrahedron, 1992, 48, 3633. Thus, a solution of sodium methoxide in methanol was prepared by adding sodium (2.12 g, 92.2 mmol) to methanol (14 ml). 2-Bromothiophene (10 g, 61.3 mmol) was added while maintaining reflux. Cuprous bromide (0.88 g, 6.1 mmol) was added and the mixture was maintained at reflux for 5.5 hours. A solution of sodium cyanide (3 g, 61.3 mmol) in water (30 ml) was added at 20–25° C. under vigorous stirring. The mixture was stirred until all solids dissolved, extracted with hexane, dried (Na2SO4), and concentrated to dryness. Distillation (90° C., 80 mm Hg) gave 2-methoxythiophene (5.35 g, 76%) as a colorless oil.

Provenance & Evidence