Acetone → Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

HRID 1886436Notes

Reaction equation

HRID 1886436 reaction equation
[O:1]1[CH2:5][CH2:4]NC1=O.Br[CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25][C:26]([CH3:28])=O>>[O:22]1[C:19]2[CH:25]=[CH:26][CH:28]=[CH:4][C:5]=2[O:1][C:8]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 739492-Oxazolidinone

Product 1

HCID 12969876Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

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.

Workup

  1. filtrationfiltered
  2. washwashed with acetone
  3. customevaporated to a brown oil
  4. customThe oil is purified by flash chromatography
  5. washeluting with 5 percent acetone in toluene
  6. customevaporated

Sources & evidence

ORD record
ord-ffcb37eed2b4447eb7e7ccc64d049bf8
Source dataset
uspto-grants-1992_09
Patent number
US05151439

Reaction notes

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