反应详情

A stirred solution of 10.0 g (0.056 mol) of 3-amino-2-methylphenylmethyl acetate and 37.4 g (0.055 mol) of furan was heated to reflux, and 8.6 g (0.084 mol) of tert-butyl nitrite was added dropwise during 30 minutes. Upon complete addition, the reaction mixture was heated under reflux an additional 1.5 hours, then cooled, and 300 mL of heptane was added. The solution was filtered through 50 g of silica gel. The silica gel was washed with 400 mL of pentane. The wash and filtrate were combined and concentrated under reduced pressure to give a residual oil which was subjected to column chromatography on silica gel, eluting with toluene. The appropriate fractions were combined and concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 4.1 g of 3-(2-furanyl)-2-methylphenylmethyl acetate, b.p. 94±2° C./0.05 mm.

1. temperatureto reflux
2. additionUpon complete addition
3. temperaturethe reaction mixture was heated
4. temperatureunder reflux an additional 1.5 hours
5. temperaturecooled
6. filtrationThe solution was filtered through 50 g of silica gel
7. washThe silica gel was washed with 400 mL of pentane
8. washThe wash
9. concentrationconcentrated under reduced pressure
10. customto give a residual oil which
11. washeluting with toluene
12. concentrationconcentrated under reduced pressure
13. customto give a residual oil
14. distillationThe oil was subjected to distillation under reduced pressure
15. distillationdistilling system