反应详情

A mixture of 2-(2-benzofuranyl)-2-hydroxyethanamine (1.0 g) and 4-[(E)-2-carbomethoxyethenyl]phenyl propan-2-one (1.13 g) was heated under reflux using a Dean and Stark head until the theoretical amount of water had been removed. The solvent was evaporated, the residue dissolved in methanol (50 ml) and sodium borohydride (0.5 g) added. The solvent was evaporated, the residue partitioned between water and ethyl acetate and the organic layer dried (magnesium sulphate). Removal of the solvent gave an oil which was chromatographed on Kieselgel 60. Elution with 2% methanol-chloroform gave N-[2-(4-[(E)-2-carbomethoxyethenyl]phenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine, as a 54:46 mixture of diastereoisomers, m.p. 85-89 (cyclohexane).

1. temperaturewas heated
2. temperatureunder reflux
3. customhad been removed
4. customThe solvent was evaporated
5. dissolutionthe residue dissolved in methanol (50 ml)
6. additionsodium borohydride (0.5 g) added
7. customThe solvent was evaporated
8. customthe residue partitioned between water and ethyl acetate
9. dry with materialthe organic layer dried (magnesium sulphate)
10. customRemoval of the solvent
11. customgave an oil which
12. customwas chromatographed on Kieselgel 60
13. washElution with 2% methanol-chloroform