反应详情

To a flask containing 4-methylnicotinic acid 1.5 hydrochloride (9.6 g, 55.3 mmol), dissolved in dry absolute ethanol (120 mL) was added concentrated sulfuric acid (6 mL) via drop-wise addition. The material was heated to reflux temperature and stirred over night. The flask was cooled to ambient and about 85% of the solvent was removed on the rotovap. Ethyl acetate (40 mL) was added and the material was basified via drop-wise addition of an aqueous saturated sodium bicarbonate solution. Ethyl acetate (40 mL) and water (20 mL) was added and the material was shaken in a separatory funnel. The ethyl acetate phase was collected and washed with brine (60 mL). The aqueous phases were back extracted with ethyl acetate (2×50 mL), the organic phases were combined, dried (MgSO4), filtered and stripped affording ethyl-4-methylnicotinoate as a brown mobile oil. MS (M+H)+=166.

1. additionvia drop-wise addition
2. temperatureThe material was heated
3. temperatureto reflux temperature
4. customwas removed on the rotovap
5. additionEthyl acetate (40 mL) was added
6. additionthe material was basified via drop-wise addition of an aqueous saturated sodium bicarbonate solution
7. additionEthyl acetate (40 mL) and water (20 mL) was added
8. stirringthe material was shaken in a separatory funnel
9. customThe ethyl acetate phase was collected
10. washwashed with brine (60 mL)
11. extractionThe aqueous phases were back extracted with ethyl acetate (2×50 mL)
12. dry with materialdried (MgSO4)
13. filtrationfiltered