反应详情

A mixture of 4-(E)-(2-carbomethoxyethenyl)phenylpropan-2-one (2.18 g) and 2-hydroxy-2-phenylethanamine (1.37 g) was refluxed in benzene under a Dean and Stark apparatus until the theoretical amount of water had been collected. The solvent was evaporated, methanol added, and sodium borohydride (1.0 g) added portionwise at room temperature. The solution was left to stir for 0.5 h, and solvent removed. Water was added, the mixture extracted with ether and the combined ether layers dried (MgSO4). Removal of the solvent gave the title compound, isolated as a 1:1 mixture of diastereoisomers, as the hemi-fumarate hemihydrate mp 99°-100.5° (ethyl acetate). τ (DMSO) 8.95 (3H, d, J=6 Hz), 6.4-7.5 (5H, m), 6.31 (3H, s), 5.2-4.9 (1H, m), 3.45 (1H, d, J=16 Hz+2H, s), 2.15-2.9 (10H, m), 1.6 (4H, s, disappears with D2O).

1. customhad been collected
2. customThe solvent was evaporated
3. additionmethanol added
4. additionsodium borohydride (1.0 g) added portionwise at room temperature
5. waitThe solution was left
6. customsolvent removed
7. additionWater was added
8. extractionthe mixture extracted with ether
9. dry with materialthe combined ether layers dried (MgSO4)
10. customRemoval of the solvent