반응 #2028459

반응 방정식

5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine

sodium hydride

toluene acetone

→

5-ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine

수율 81.1%

용매

toluene

반응 조건

후처리

1. 1
   기타were removed by distillation
2. 2
   workup.ADDITIONwater (10 mL) and ethyl acetate (20 mL) were added
3. 3
   기타The organic phase was separated
4. 4
   추출the aqueous layer extracted with ethyl acetate (2×20 mL)
5. 5
   세척the combined organic extracts were washed with brine (10 mL)
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude product was purified by silica gel column chromatography with ethyl acetate as eluant

실험 절차

5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine (200 mg, 0.77 mmol) was dissolved in toluene (20 mL) and catalytic sodium hydride (5 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture were removed by distillation. The mixture was cooled to 25° C. and water (10 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the aqueous layer extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with brine (10 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate as eluant to afford 5-ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine as a solid (125 mg, 81%). M.p. 83°-84° C.; 1H NMR (CDCl 3, 300 MHz): δ8.69 (d, J=2 Hz, 1H), 8.46 (d, J=2 Hz, 1H), 7.62 (t, J=2 Hz, 1H), 4.57 (dd, J=7, 6 Hz, 1H), 3.28 (s, 1H), 2.70 (s, 3H), 2.45-2.65 (m, 3H), 1.88 (m, 1H).

출처