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

HRID 1492173Notes

Reaction equation

HRID 1492173 reaction equation
ClC1C=C([C@H]2OC(=O)N([C@H](C)C[C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=3)C2)C=CC=1.Br[CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:22]1[C:19]2[CH:20]=[CH:21][CH:16]=[CH:17][C:18]=2[O:23][C:26]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 9884666(R,R)-5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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-b2040126aba24666be2f5b094236ec2f
Source dataset
uspto-grants-1994_12
Patent number
US05373020

Reaction notes

Loading…