反应详情

A mixture of 8-bromomethyl-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone (0.46 g), 4-methyl-1-tritylimidazole (0.49 g) and acetonitrile (2 ml) was heated under reflux for 18 h, then evaporated to dryness. The residue was treated with glacial acetic acid (4 ml) and water (1 ml), and the mixture was heated at 90° for 0.5 h. The mixture was diluted with water (20 ml) and washed with diethyl ether. The aqueous phase was separated, basified with potassium hydrogen carbonate and extracted twice with ethyl acetate. The extracts were combined, dried and evaporated to dryness, and the residue was purified by flash chromatography, eluting with methanol:ethyl acetate, 1:99 v/v, to give 1,1-dimethyl-8-(5-methylimidazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 88°-91°.

1. temperaturewas heated
2. temperatureunder reflux for 18 h
3. customevaporated to dryness
4. additionThe residue was treated with glacial acetic acid (4 ml) and water (1 ml)
5. temperaturethe mixture was heated at 90° for 0.5 h
6. additionThe mixture was diluted with water (20 ml)
7. washwashed with diethyl ether
8. customThe aqueous phase was separated
9. extractionextracted twice with ethyl acetate
10. customdried
11. customevaporated to dryness
12. customthe residue was purified by flash chromatography
13. washeluting with methanol