Reaction #410112

Reaction equation

hydrochloric acid

Diethyl oxalate

potassium ethoxide

4-benzyloxyacetophenone

→

ethyl 4-benzyloxypheyl-2,4-dioxobutanoate

Yield 97.1%

Solvents

ether

Conditions

Workup

1. 1
   workup.WAITAfter standing at room temperature for 18 hours
2. 2
   Otherthe organic phase separated
3. 3
   WashThe organic phase is washed with water
4. 4
   Dryingdried over magnesium sulphate
5. 5
   Otherevaporated

Procedure

Diethyl oxalate (17.7 g) is added in one portion to a stirred suspension of potassium ethoxide (10.2 g) in anhydrous ether (1000 mL). The stirred mixture is cooled to 0° C., treated with 4-benzyloxyacetophenone (25 g) portionwise, and stirring continued for 3 hours. After standing at room temperature for 18 hours the reaction mixture is poured onto 1 N hydrochloric acid (500 mL) and the organic phase separated. The organic phase is washed with water, dried over magnesium sulphate and evaporated to give ethyl 4-benzyloxypheyl-2,4-dioxobutanoate (35 g).

Source