反应 #6948

反应方程式

methyl iodide

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

CS2

NH4Cl

1-bromo-butan-2-one

→

desired product

收率 32.1%

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

收率 32.1%

溶剂

DMF

反应条件

后处理

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
   温度then warmed to ambient temperature
4. 4
   萃取The solution was extracted with ethyl acetate (200 mL×3)
5. 5
   干燥the combined organic layers were dried over Na2SO4
6. 6
   浓缩then concentrated in vacuo
7. 7
   其他Purification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate)

实验过程

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).

来源