Potassium Carbonate → Methyl 2-hydroxy-3-methylbutanoate

HRID 847116Notes

Reaction equation

HRID 847116 reaction equation
[CH3:1][C:2]1[CH:7]=C(C)N=C(S(C)(=O)=O)N=1.C(=O)([O-])[O-:14].[K+].[K+].[C:19]([O:22][CH2:23]C)(=[O:21])[CH3:20].CCCCCC>CC(C)=O>[OH:14][CH:20]([CH:2]([CH3:7])[CH3:1])[C:19]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27723824,6-Dimethyl-2-methylsulfonylpyrimidineHCID 21226206Ethyl acetate hexane

Product 1

HCID 552631Methyl 2-hydroxy-3-methylbutanoateYield 42%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.5g of the product of (b) and 2.llg (0.011 moles) of 4,6-dimethyl-2-methanesulphonyl pyrimidine were dissolved in 20ml acetone. 1.6g of potassium carbonate were added and the reaction mixture refluxed for 4 hours. Following thin layer chromatography to establish that the reaction had reached completion, the mixture was evaporated to dryness and 10ml water added. Solvent extraction using chloroform followed and the chloroform extracts were dried over anhydrous sodium sulphate and the solvent evaporated off. The oil resulting was subjected to flash column chromatography using ethyl acetate: hexane (1:1) as eluant to yield 1.1g (yield 42%) of the title compound as a colourless oil.

Workup

  1. temperaturethe reaction mixture refluxed for 4 hours
  2. customthe mixture was evaporated to dryness and 10ml water
  3. additionadded
  4. extractionSolvent extraction
  5. dry with materialthe chloroform extracts were dried over anhydrous sodium sulphate
  6. customthe solvent evaporated off
  7. customThe oil resulting

Sources & evidence

ORD record
ord-cf79931c56a949f79b58fb9cfb194278
Source dataset
uspto-grants-1992_08
Patent number
US05139563

Reaction notes

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