Reaction #5674

Reaction equation

oxazolidinone

diethyl bromomalonate

potassium carbonate

acetone

→

1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Washwashed with acetone
3. 3
   Otherevaporated to a brown oil
4. 4
   OtherThe oil is purified by flash chromatography
5. 5
   Washeluting with 5 percent acetone in toluene
6. 6
   Otherevaporated

Procedure

A mixture of 240 mg of the above oxazolidinone, 234 mg of diethyl bromomalonate, 450 mg of anhydrous potassium carbonate and 10 ml of acetone is stirred overnight, filtered, washed with acetone and evaporated to a brown oil. The oil is purified by flash chromatography, eluting with 5 percent acetone in toluene. The pure fractions are combined and evaporated giving 237 mg of (R,R)-5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester as a colorless oil.

Source