Methanol → Butanoic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, methyl ester, (S)-

HRID 1917513

Reaction equation

HRID 1917513 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][CH2:12][O:11]C1=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15](=[O:18])([O-])[O-:16].[K+].[K+].[CH3:21]O>>[Si:1]([O:8][C@@H:9]([CH2:13][CH2:12][OH:11])[C:15]([O:16][CH3:21])=[O:18])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 10965951(S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactone

Product 1

HCID 11107713Butanoic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, methyl ester, (S)-

Procedure

To a solution of (S)-3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one (91b, 6 g, 27.8 mmol) in methanol (40 mL) was added potassium carbonate (500 mg, 3.6 mmol). The reaction was refluxed overnight. The methanol was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with H2O×2 and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate (91c, 3.9 g, 15.7 mmol) as a clear oil. [M+H] calc'd for C11H24O4Si, 249; found, 249.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customThe methanol was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with H2O×2
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6d0eae1174934a4b8a7f33756245f8a5
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Linked notes

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