反応 #5998

反応方程式

water

sodium ethoxide

diethyl acetamidomalonate

benzyl chloride

3-(Chloromethyl)-2-phenylmethoxyanisole

→

pure crystalline product

収率 66.4%

2-(Acetylamino)-2-[[3-methoxy-2-(phenylmethoxy) -phenyl]methyl]-propanedioic acid, diethyl ester

収率 66.4%

溶媒

acetic acid

ethanol

ethanol

—

Petroleum ether

ethanol

反応条件

後処理

1. 1
   温度the mixture is heated
2. 2
   温度at reflux for 2 hours
3. 3
   その他The supernatant is decanted from the separated gum
4. 4
   workup.DISSOLUTIONThe gum is dissolved in 2 L of ether
5. 5
   乾燥the solution dried (magnesium sulfate)
6. 6
   濃縮concentrated to ca 300 mL volume

実験手順

A quantity of 136.20 g (0.42 mole) of 21 wt.% sodium ethoxide in ethanol is added to a stirred solution of 90.14 g (0.415 mole) of diethyl acetamidomalonate (Aldrich) in 800 mL of absolute ethanol. A solution of the benzyl chloride derivative of Example 38 in 500 mL of absolute ethanol is added and the mixture is heated at reflux for 2 hours. The cooled mixture is poured into 4 L of ice and water containing 20.0 g of glacial acetic acid. The supernatant is decanted from the separated gum. The gum is dissolved in 2 L of ether, the solution dried (magnesium sulfate), and concentrated to ca 300 mL volume. Petroleum ether (100 mL) is added to precipitate 107.1 g (66.4% yield) of pure crystalline product; mp 94°-96° C.

出典