Water → HCID 57713984, compound

HRID 1984555Notes

Reaction equation

HRID 1984555 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:5]([O:7]C)=[O:6].C(=O)([O-])[O-:15].[Cs+].[Cs+].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4]([OH:15])([CH2:9][CH:10]([CH3:12])[CH3:11])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 170218Propanedioic acid, (2-methylpropyl)-, dimethyl ester

Product 1

HCID 57713984HCID 57713984, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Air was bubbled for 1 hour at room temperature through a suspension of 0.5 g (3 mmol) dimethyl-(2-methylpropyl)malonate and 1.73 g (5 mmol) cesium carbonate in 7 ml dimethylformamide. Stirring was continued at room temperature for 24 hours. 25 ml water was added and the mixture was extracted with diethylether. Acidification with aqueous 1 N hydrochloric acid to pH=1 and extraction with ethylacetate yielded 0.42 g (83%) (R/S)-2-hydroxy-2-isobutyl-malonic acid monomethyl ester, MS (m/e): 189.4 (M−H)−.

Workup

  1. extractionthe mixture was extracted with diethylether
  2. extractionAcidification with aqueous 1 N hydrochloric acid to pH=1 and extraction with ethylacetate

Sources & evidence

ORD record
ord-8a7354baf6054fb2b4c119c004ba30c2
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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