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

HRID 1917513

반응식

HRID 1917513 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d0eae1174934a4b8a7f33756245f8a5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618290B2

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