Reaktion #1446020

Reaktionsgleichung

sodium cyanide

sodium

methanol

methanol

2-Bromothiophene

→

sodium methoxide

2-methoxythiophene

Ausbeute 76.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige2-Methoxythiophene was prepared by the procedures
2. 2
   Temperaturwhile maintaining
3. 3
   Temperaturreflux
4. 4
   Temperaturthe mixture was maintained
5. 5
   Temperaturat reflux for 5.5 hours
6. 6
   workup.DISSOLUTIONdissolved
7. 7
   Extraktionextracted with hexane
8. 8
   Trocknendried (Na2SO4)
9. 9
   Einengenconcentrated to dryness
10. 10
    workup.DISTILLATIONDistillation (90° C., 80 mm Hg)

Vorschrift

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.

Quelle