반응 #11554

반응 방정식

ammonium chloride

Diisopropylamine

butyllithium hexane

tetrahydrofuran

acetonitrile

→

3-hydroxy-3-(4-pyridyl)propionitrile

수율 63.5%

반응 조건

후처리

1. 1
   온도The mixture was cooled to −80° C. again
2. 2
   workup.WAITafter 20 minutes
3. 3
   workup.ADDITION4-pyridinecarboxyaldehyde (758 mg, 7.08 mmol) was added dropwise
4. 4
   workup.WAITover 10 minutes
5. 5
   workup.WAITAfter 50 minutes
6. 6
   온도the temperature was raised to room temperature
7. 7
   추출The whole was continuously extracted (ethyl acetate and water) for four days
8. 8
   건조The organic layer was dried over anhydrous magnesium sulfate
9. 9
   기타the solvent was evaporated under reduced pressure
10. 10
    기타the residue was purified by silica gel column chromatography

실험 절차

Diisopropylamine (1.98 g, 19.6 mmol) was added dropwise to a solution of a butyllithium/hexane solution (10.5 ml, 16.8 mmol) in anhydrous tetrahydrofuran (20 ml) at −80° C. over five minutes, the temperature was raised to 0° C., and the mixture was stirred for 30 minutes. The mixture was cooled to −80° C. again, then acetonitrile (573 mg, 14.0 mmol) was added dropwise to the mixture over seven minutes, and after 20 minutes, 4-pyridinecarboxyaldehyde (758 mg, 7.08 mmol) was added dropwise thereto over 10 minutes. After 50 minutes, a saturated aqueous ammonium chloride solution (20 ml) was added to the reaction mixture, and the temperature was raised to room temperature. The whole was continuously extracted (ethyl acetate and water) for four days. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 3-hydroxy-3-(4-pyridyl)propionitrile (666 mg, colorless crystals, 63.5%).

출처