Cesium carbonate → Propanedioic acid, 2-hydroxy-2-methyl-, 1-ethyl ester

HRID 1348634Notes

Reaction equation

HRID 1348634 reaction equation
[CH3:1][CH:2]([C:8]([O:10]CC)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-:14].[Cs+].[Cs+]>CN(C)C=O>[CH2:6]([O:5][C:3](=[O:4])[C:2]([OH:14])([CH3:1])[C:8]([OH:10])=[O:9])[CH3:7]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 11857Diethyl methylmalonate

Product 1

HCID 13396337Propanedioic acid, 2-hydroxy-2-methyl-, 1-ethyl esterYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.52 g (20 mmol) diethyl methylmalonate in 40 ml dimethylformamide were added 13.1 g (40 mmol) cesium carbonate. The suspension was stirred at room temperature and air was bubbled in for 1 hour. The mixture was poured into water and extracted with ethylacetate. Extraction at pH 1 with ethylacetate yielded 2.28 g (70%) 2-hydroxy-2-methyl-malonic acid monoethyl ester, light yellow liquid, MS m/e (%): 161.0 (M−H, 100).

Workup

  1. customair was bubbled in for 1 hour
  2. additionThe mixture was poured into water
  3. extractionextracted with ethylacetate
  4. extractionExtraction at pH 1 with ethylacetate

Sources & evidence

ORD record
ord-6e1c68a6d5c1454b9f9cd494cf160ec2
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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