Methanol → 2-Methoxythiophene

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.

1. custom2-Methoxythiophene was prepared by the procedures
2. temperaturewhile maintaining
3. temperaturereflux
4. temperaturethe mixture was maintained
5. temperatureat reflux for 5.5 hours
6. dissolutiondissolved
7. extractionextracted with hexane
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated to dryness
10. distillationDistillation (90° C., 80 mm Hg)

ORD record

ord-19b0ba9298b747a3b72ada2da9a78ace

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06472536B1