反応 #6948

反応方程式

methyl iodide

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

CS2

NH4Cl

1-bromo-butan-2-one

→

desired product

収率 32.1%

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

収率 32.1%

溶媒

DMF

反応条件

後処理

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
   抽出The solution was extracted with ethyl acetate (200 mL×3)
5. 5
   乾燥the combined organic layers were dried over Na2SO4
6. 6
   濃縮then concentrated in vacuo
7. 7
   その他Purification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate)

実験手順

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).

出典