4,4,4-Trifluoro-3-hydroxy-3-methylbutanoic acid → 3-(Trifluoromethyl)-3-hydroxybutyric acid methyl ester

HRID 2242389Notes

Reaction equation

HRID 2242389 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]([OH:9])([CH3:8])[CH2:4][C:5]([OH:7])=[O:6].[CH3:12][Si](C=[N+]=[N-])(C)C>CO>[CH3:12][O:6][C:5](=[O:7])[CH2:4][C:3]([C:2]([F:10])([F:11])[F:1])([OH:9])[CH3:8]

Participants

4

Reactant 2

HCID 1361684,4,4-Trifluoro-3-hydroxy-3-methylbutanoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 856464933-(Trifluoromethyl)-3-hydroxybutyric acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4,4,4-trifluoro-3-hydroxy-3-methylbutyric acid (1.81 g, 10.0 mmol) in methanol (10 ml) was added (trimethylsilyl)diazomethane (10 ml), dropwise. The reaction was then stirred at room temperature for 4 h. Removal of the solvent afforded the crude 3-(trifluoromethyl)-3-hydroxybutyric acid methyl ester as a yellow oil (1.92 g, 100%).

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-263381dfbe584384bb7f02dbf1c5b9aa
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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