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-e68399a59e98448abfbcb05e435ff2fd

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06184242B2