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

HRID 1886879

Reaktionsgleichung

Reaktionsgleichung von HRID 1886879
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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:

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d2b4c8deffd54afd8b5a3ad802662951
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501709B2

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