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

HRID 1452060

Reaction equation

HRID 1452060 reaction equation
[O:1]1[CH2:5][CH2:4]NC1=O.[CH2:7]([O:9][C:10](=[O:18])[CH:11](Br)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:8].[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:11]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([O:9][CH2:7][CH3:8])=[O:18]

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 0.240 g of the above oxazolidinone, 0.250 g of diethylbromomalonate, 0.500 g 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% acetone/toluene. The pure fractions are combined and evaporated giving (S,R)-5-(1-naphthyloxymethyl)-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% acetone/toluene
  6. customevaporated

Sources & evidence

ORD record
ord-4e8b0a2bc98544b3b014761d8d87e044
Source dataset
uspto-grants-1997_02
Patent number
US05606069

Linked notes

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