反应详情

30 ml of benzene, 0.4 g (4 mmol) of 3-piperidinol and 1.0 g (4 mmol) of methyl benzilate were put into a 50 ml 3-mouth flask equipped with a stirrer, a reflux condenser, and a molecular sieve 4A (15 g) tube and a soda lime tube for trapping methanol from out of the solvent that drips down through the reflux condensation, and the mixture was refluxed by heating while stirring. After all of the methyl benzilate had dissolved, 20 mg of sodium methoxide (made by Aldrich) was added to the solution and reaction was carried out for 3 hours. After the reaction had been completed, the reaction liquid was cooled to room temperature, and then 50 ml of 1N hydrochloric acid was added, and the organic solvent layer was removed. The aqueous solution layer obtained was washed twice with 50 ml of ether, and was then made basic using a 28% ammonium hydroxide aqueous solution. The aqueous solution was subjected to ether extraction, the ether layer obtained was washed twice with 50 ml of water, and then drying was carried out using anhydrous potassium carbonate. After removing the drying agent, the solvent was evaporated off under reduced pressure, thus obtaining an oily residue, and then this residue was recrystallized from ether-hexane, thus obtaining 0.5 g of (±)3-piperidyl benzilate ((±)3-PB) as crystals (yield 40%).

1. customequipped with a stirrer, a reflux condenser
2. customdown through the reflux condensation
3. temperaturethe mixture was refluxed
4. temperatureby heating
5. customthe reaction liquid
6. customthe organic solvent layer was removed
7. customThe aqueous solution layer obtained
8. washwas washed twice with 50 ml of ether
9. extractionThe aqueous solution was subjected to ether extraction
10. customthe ether layer obtained
11. washwas washed twice with 50 ml of water
12. customdrying
13. customAfter removing the drying agent
14. customthe solvent was evaporated off under reduced pressure
15. customthus obtaining an oily residue
16. customthis residue was recrystallized from ether-hexane