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

HRID 656614

Reaction equation

HRID 656614 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-8a37422d9f144ce29c1d706d507c7f1d
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Linked notes

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