反应详情

A solution of 5-acetyl-benzofuran-7-carbaldehyde (471 mg) in dry toluene (40 ml) was treated with sodium triacetoxyborohydride (1.12 ml) and heated at reflux for 5.5 h. The reaction mixture was poured into 8% sodium bicarbonate (40 ml) and the phases were separated. The aqueous phase was extracted with ethyl acetate (40 ml), the combined organic phases were dried, filtered, and the filtrate evaporated in vacuo to give a yellow gum. Purification by FCC eluted with hexane:ethyl acetate (2:1→1:1) gave the title compound as a pale yellow oil (275 mg) which slowly solidified.

1. temperatureheated
2. temperatureat reflux for 5.5 h
3. customthe phases were separated
4. extractionThe aqueous phase was extracted with ethyl acetate (40 ml)
5. customthe combined organic phases were dried
6. filtrationfiltered
7. customthe filtrate evaporated in vacuo
8. customto give a yellow gum
9. customPurification by FCC
10. washeluted with hexane:ethyl acetate (2:1→1:1)