반응 #6948

반응 방정식

methyl iodide

3-oxo-3-pyridin-3-yl-propionitrile

CS2

NH4Cl

1-bromo-butan-2-one

→

desired product

수율 32.1%

1-(4-Methyl-5-methylsulfanyl-3-pyridin-3-yl-thiophen-2-yl)-propan-1-one

수율 32.1%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred for another 30 minutes
2. 2
   workup.STIRRINGThe resulting mixture was stirred for another 30 minutes
3. 3
   온도then warmed to ambient temperature
4. 4
   추출The solution was extracted with ethyl acetate (200 mL×3)
5. 5
   건조the combined organic layers were dried over Na2SO4
6. 6
   농축then concentrated in vacuo
7. 7
   기타Purification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate)

실험 절차

To a solution of 3-oxo-3-pyridin-3-yl-propionitrile (11.9 mmol) in DMF (100 mL) was added CS2 (0.90 ml, 15.0 mmol) at 0° C. The reaction was stirred at 0° C. for 45 minutes under nitrogen then 1-bromo-butan-2-one (1.79 g, 11.8 mmol) was added via a syringe at 0° C. The reaction was stirred for another 30 minutes then methyl iodide (1.69 g, 11.8 mmol) was added via syringe at 0° C. The resulting mixture was stirred for another 30 minutes then warmed to ambient temperature and poured into saturated aqueous NH4Cl solution (300 mL). The solution was extracted with ethyl acetate (200 mL×3) and the combined organic layers were dried over Na2SO4 then concentrated in vacuo. Purification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate) afforded 1.05 g desired product. 1H NMR (CDCl3): δ 8.8 (d, 1H), 8.6 (s, 1H), 7.8 (d, 1H), 7.5 (dd, 1H), 2.8 (s, 3H), 2.3 (q, 2H), 1.0 (t, 3H).

출처