反応 #46664

反応方程式

sodium hydrogencarbonate

diethyl methylmalonate

sodium hydride

4-chloropicolyl hydrochloride

→

diethyl 2-methyl-2-(4-pyridylmethyl)malonate

溶媒

N,N-dimethylformamide

N,N-Dimethylformamide

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.WAITAfter one hour
3. 3
   抽出the whole was extracted with diethyl ether (400 ml)
4. 4
   洗浄The organic layer was washed with water (100 ml) and saturated brine (50 ml) successively
5. 5
   乾燥dried over magnesium sulfate
6. 6
   濃縮concentrated under reduced pressure

実験手順

N,N-Dimethylformamide (143 ml) was added to sodium hydride (5.36 g, 134 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cooling. A solution of diethyl methylmalonate (11.7 g, 67.1 mmol) in N,N-dimethylformamide (40 ml) was added dropwise to the mixture over five minutes, after 10 minutes, 4-chloropicolyl hydrochloride (10.0 g, 61.0 mmol) was added thereto little by little over five minutes, and the temperature was raised to room temperature. After one hour, a saturated aqueous sodium hydrogencarbonate solution (500 ml) was added to the reaction mixture, and the whole was extracted with diethyl ether (400 ml). The organic layer was washed with water (100 ml) and saturated brine (50 ml) successively, dried over magnesium sulfate and concentrated under reduced pressure to give diethyl 2-methyl-2-(4-pyridylmethyl)malonate (17.2 g, quantitatively, containing sodium hydride oil) as a brown oily matter.

出典