Benzoyl chloride → (S)-beta-Benzoyloxy-gamma-butyrolactone

HRID 1886879

반응식

HRID 1886879 반응식
[OH:1][CH:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.[C:8](Cl)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]>N1C=CC=CC=1>[C:8]([O:1][C@@H:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 7412Benzoyl chlorideHCID 956523,4-Dihydroxybutanoic acid gamma-lactone

생성물 1

HCID 10058799(S)-beta-Benzoyloxy-gamma-butyrolactone수율 89%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To the solution of (S)-(3-Hydroxy-γ-butyrolactone (1.0 g, 9.8 mmol) in 25 mL pyridine was added dropwise BzCl (1.4 mL, 12.2 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was concentrated and coevaporated with toluene two times in vacuo. The residue was partitioned between H2O (15 mL) and EtOAc (40 mL). The organic layer was washed with water and brine, and concentrated in vacuo. The residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:1) to afford 101 (1.78 g, 8.6 mmol) as a white solid, in 89% yield, which was characterized as follows:

후처리

  1. concentrationThe reaction was concentrated
  2. customThe residue was partitioned between H2O (15 mL) and EtOAc (40 mL)
  3. washThe organic layer was washed with water and brine
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:1)

출처 및 근거

ORD 기록
ord-d2b4c8deffd54afd8b5a3ad802662951
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501709B2

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