Reaction #362829

Reaction equation

diethyl 4-aminobenzylacetamidomalonate

sodium acetate

2,5-dimethoxytetrahydrofuran

→

solid

Diethyl 4-(1-pyrrolyl)benzylacetamidomalonate

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturewhich is maintained under nitrogen
2. 2
   Temperaturecooled down
3. 3
   Extractionextracted with 100 ml of dichloromethane and 100 ml of distilled water
4. 4
   OtherThe aqueous phase is separated off
5. 5
   Washwashed with 3 times 100 ml of dichloromethane
6. 6
   Washwashed with 100 ml of water
7. 7
   Otherwith 100 ml of a saturated solution of NaCl, separated off
8. 8
   Dryingdried over magnesium sulphate
9. 9
   Filtrationthe phases are filtered
10. 10
    Otherevaporated to dryness under reduced pressure (50 kPa) in order

Procedure

4,6 g of diethyl 4-aminobenzylacetamidomalonate in 104 ml of acetic acid are placed in a three-necked flask which is maintained under nitrogen. 7.02 g of sodium acetate are added, followed by 1.87 ml of 2,5-dimethoxytetrahydrofuran. The mixture is heated at 65° C. for 1 h 15 min, then cooled down and extracted with 100 ml of dichloromethane and 100 ml of distilled water. The aqueous phase is separated off after settling and then washed with 3 times 100 ml of dichloromethane. The organic phases are combined, washed with 100 ml of water and then with 100 ml of a saturated solution of NaCl, separated off after settling and then dried over magnesium sulphate; the phases are filtered and then evaporated to dryness under reduced pressure (50 kPa) in order to yield 6.2 g of a solid which is purified by flash chromatography (eluent CH2Cl2/acetone 75/25 by volume). This results in 3.57 g of diethyl 4-(1-pyrrolyl)benzylacetamidomalonate in the form of a beige solid which melts at 110° C.

Source