Benzoyl chloride → 2(S)-(benzoyloxymethyl)-1,3-oxathiolane

HRID 1689575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689575
[OH:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[C:8]([O:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 46244897HCID 46244897, Verbindung

Produkt 1

HCID 596089912(S)-(benzoyloxymethyl)-1,3-oxathiolaneAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2(S)-(Hydroxymethyl)-1,3-oxathiolane (0.25 mmol, 30 mg, 1.0 equiv.) recovered from Example 3 was treated with benzoyl chloride (0.25 mmol, 35 mg, 1.0 equiv.), triethylamine (0.25 mmol, 25 mg, 1.0 equiv.) in dichloromethane (1 mL) at ambient temperature while monitoring the reaction progress by TLC. After 1 h, the reaction was extracted with saturated ammonium chloride solution and brine. The organic phase was concentrated and chromatographed on silica gel to give 2(S)-(benzoyloxymethyl)-1,3-oxathiolane (25 mg, 44.6%).

Aufarbeitung

  1. extractionthe reaction was extracted with saturated ammonium chloride solution and brine
  2. concentrationThe organic phase was concentrated
  3. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2b1d43f87cb148e4864d59d7e1a195a5
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153416B2

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