Water → HCID 57434480, compound

HRID 1984551Notes

Reaction equation

HRID 1984551 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([CH2:11][CH2:12][CH3:13])[C:6]([O:8]CC)=[O:7])[CH3:2].C(=O)([O-])[O-:16].[Cs+].[Cs+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5]([OH:16])([CH2:11][CH2:12][CH3:13])[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 16552Diethyl propylmalonate

Product 1

HCID 57434480HCID 57434480, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Air was bubbled for 1 hour at room temperature through a suspension of 15.0 g (72.7 mmol) diethylpropylmalonate and 47.6 g (145 mmol) cesium carbonate in 120 ml dimethylformamide. At 10-20° C. 150 ml water were added and stirring was continued at room temperature for 3 hours. Most of the dimethylformamide was then removed by vacuum distillation at 35° C. bath temperature. 1 l water was added and extraction with diethylether yielded 11.7 g 2-hydroxy-2-propyl-malonic acid monoethylester, MS (m/e): 189.1 (M−H)−.

Workup

  1. customAt 10-20° C
  2. customMost of the dimethylformamide was then removed by vacuum distillation at 35° C. bath temperature
  3. addition1 l water was added
  4. extractionextraction with diethylether

Sources & evidence

ORD record
ord-ebe6ac9fe9fe4d9bb91506afcca64c12
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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