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

HRID 1886879

反応式

HRID 1886879 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 10058799(S)-beta-Benzoyloxy-gamma-butyrolactone収率 89%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-d2b4c8deffd54afd8b5a3ad802662951
出典データセット
uspto-grants-2013_08
特許番号
US08501709B2

関連ノート

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