Ethyl bromoacetate → Diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinate

HRID 1788638Notes

Reaction equation

HRID 1788638 reaction equation
[CH2:1]([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:2][CH3:3].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.O>[CH2:1]([C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 16552Diethyl propylmalonateHCID 24758Sodium hydride

Product 1

HCID 20075591Diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinateYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Diethyl prop-1-ylmalonate (70.23 g) was added dropwise to a stirred suspension of sodium hydride (8.35 g) in dimethylformamide (400 ml) under an atmosphere of nitrogen at 10° to 15° C. Following the addition, the mixture was allowed to stir at room temperature until effervescence ceased. The resulting clear solution was cooled again and ethyl bromoacetate (58.06 g) was added. The mixture was heated at 70° C. for 2 hours then allowed to cool, diluted with water, and extracted with ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated to give almost pure diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinate (97.35 g, 97%) as a pale yellow liquid.

Workup

  1. additionthe addition
  2. temperatureThe resulting clear solution was cooled again
  3. temperatureThe mixture was heated at 70° C. for 2 hours
  4. temperatureto cool
  5. extractionextracted with ether
  6. washThe extracts were washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dc9ee49832794fa68de60f9cd2a0a860
Source dataset
uspto-grants-1987_08
Patent number
US04684396

Reaction notes

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