反应详情

Sodium triacetoxyborohydride (5.46 g, 26 mmol) is added in small portions to a stirred solution of aniline (2.0 g, 21.5 mmol) and phenylacetaldehyde (2.83 g, 24 mmol) in dry DMF/MeOH/AcOH (87:10:3, 120 ml). After stirring at rt for 90 min, the volatiles are removed under reduced pressure. The residue is dissolved in dichloromethane (200 ml) and extracted twice with 1 N HCl. The combined aqueous layers are washed with EtOAc, then ammonium hydroxide solution is added to pH 9, and the mixture is extracted with dichloromethane. The solvent is evaporated, and the crude product is purified by silica gel chromatography (hexane/EtOAc, 5:1) affording pure title compound as a yellow oil.

1. customthe volatiles are removed under reduced pressure
2. dissolutionThe residue is dissolved in dichloromethane (200 ml)
3. extractionextracted twice with 1 N HCl
4. washThe combined aqueous layers are washed with EtOAc
5. additionammonium hydroxide solution is added to pH 9
6. extractionthe mixture is extracted with dichloromethane
7. customThe solvent is evaporated
8. customthe crude product is purified by silica gel chromatography (hexane/EtOAc, 5:1)