Reaction #362826

Reaction equation

diethyl acetamidomalonate

4-(tert-butyl)benzyl bromide

toluene

sodium hydride

→

diethyl 4-(tert-butyl)benzylacetamidomalonate

Yield 68.5%

Solvents

water

ethanol

ethanol

—

suspension

Conditions

Workup

1. 1
   Otheris surmounted by a condenser
2. 2
   TemperatureAfter it has been cooled down
3. 3
   OtherThe organic phase is decanted
4. 4
   Washthe aqueous phase is washed with 3 times 50 ml of diethyl ether
5. 5
   Washwashed with water
6. 6
   Dryingdried over sodium sulphate
7. 7
   Filtrationfiltration and concentration under reduced pressure
8. 8
   Otherthe product is crystallized in petroleum ether in order

Procedure

25 g of 4-(tert-butyl)benzyl bromide, 50 ml of anhydrous toluene and 3.1 g of sodium hydride in 80% suspension in oil are added to a three-necked flask which is surmounted by a condenser, followed by 21.8 g of diethyl acetamidomalonate. The mixture is heated at 110° C. for 17 h. After it has been cooled down, 15 ml of absolute ethanol, then 15 ml of 50% ethanol and then 50 ml of water are added slowly to it using a dropping funnel. The organic phase is decanted and the aqueous phase is washed with 3 times 50 ml of diethyl ether. The organic phases are combined, washed with water and then dried over sodium sulphate. Following filtration and concentration under reduced pressure, the product is crystallized in petroleum ether in order to yield 25 g of diethyl 4-(tert-butyl)benzylacetamidomalonate in the form of a white solid which melts at 80° C.

Source