反应详情

温度

0 °C

To a solution of 3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzaldehyde (10 g) and 2-methoxybenzylamine (6 g) in toluene (150 mL) was added TsOH (100 mg). The mixture was heated at reflux in a Dean-Stark apparatus for a couple of hours. About 1 mL water was displaced. The reaction was checked by TLC, iso-hexane/EtOAc (4/1, Rf ˜0.5). The mixture was cooled and washed with aqueous bicarbornate, then concentrated in vacuo. The residue was azeotroped twice with toluene and was taken up in ethanol (150 ml). The solution was cooled to 0° C. and sodium borohydride (1.65 g) was added slowly. The reaction was left to warm to room temperature and was stirred overnight. Water was added (150 mL) and ethanol removed under vacuum. The residue was partitioned between aqueous bicarbonate and ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to give a yellow oil (6.5 g). The material was used in the next step without further purification.

1. temperatureThe mixture was heated
2. temperatureat reflux in a Dean-Stark apparatus for a couple of hours
3. temperatureThe mixture was cooled
4. washwashed with aqueous bicarbornate
5. concentrationconcentrated in vacuo
6. customThe residue was azeotroped twice with toluene
7. additionsodium borohydride (1.65 g) was added slowly
8. waitThe reaction was left
9. temperatureto warm to room temperature
10. additionWater was added (150 mL) and ethanol
11. customremoved under vacuum
12. customThe residue was partitioned between aqueous bicarbonate and ethyl acetate
13. dry with materialThe organic layers were dried over sodium sulfate
14. concentrationconcentrated in vacuo