反应详情

A mixture of methyl 3-bromomethyl-5-(1-cyano-1-methylethyl)benzoate (0.7 g), 4-methyl-1-tritylimidazole (0.8 g) and acetonitrile (2 ml) was heated under reflux for 48 h, then evaporated to dryness. The residue of 3-[3-(1-cyano-1-methylethyl)-5-methoxycarbonylbenzyl]-4-methyl-1-tritylimidazolium bromide was washed with diethyl ether (2×10 ml), and the residue was treated with glacial acetic acid (4 ml) and water (1 ml) and heated at 90° for 15 minutes. The mixture was diluted with water (20 ml), and washed with diethyl ether, and the aqueous phase was basified with 10N aqueous sodium hdroxide and extracted three times with ethyl acetate. The extracts were combined and evaporated to dryness, and the residue was purified by flash column chromatography, eluting with methanol:chloroform (1:49 by volume), to give methyl 5-(1-cyano-1-methylethyl)-3-(5-methylimidazol-1-ylmethyl)benzoate, mp 101°-104°.

1. temperaturewas heated
2. temperatureunder reflux for 48 h
3. customevaporated to dryness
4. washThe residue of 3-[3-(1-cyano-1-methylethyl)-5-methoxycarbonylbenzyl]-4-methyl-1-tritylimidazolium bromide was washed with diethyl ether (2×10 ml)
5. additionthe residue was treated with glacial acetic acid (4 ml) and water (1 ml)
6. temperatureheated at 90° for 15 minutes
7. additionThe mixture was diluted with water (20 ml)
8. washwashed with diethyl ether
9. extractionextracted three times with ethyl acetate
10. customevaporated to dryness
11. customthe residue was purified by flash column chromatography
12. washeluting with methanol:chloroform (1:49 by volume)