Benzoyl chloride → 6-Oxobicyclo[3.2.0]heptan-2-yl benzoate

HRID 15186

Reaktionsgleichung

Reaktionsgleichung von HRID 15186
[OH:1][CH:2]1[CH2:8][CH2:7][CH:6]2[CH:3]1[CH2:4][C:5]2=[O:9].CCN(CC)CC.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[C:17]([O:1][CH:2]1[CH2:8][CH2:7][CH:6]2[CH:3]1[CH2:4][C:5]2=[O:9])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 134438072-Hydroxybicyclo[3.2.0]heptan-6-one

Produkt 1

HCID 592595756-Oxobicyclo[3.2.0]heptan-2-yl benzoateAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of compound 1G (1.9 g, 15.1 mmol) in CH2Cl2 (10 mL) at 0° C. under nitrogen were added Et3N (3.1 mL, 22.2 mmol) and benzoyl chloride (2.33 g, 16.6 mmol). The reaction was stirred at 0° C. for 60 min and RT for 30 min, then quenched with water. The product was extracted with CH2Cl2, the organics were washed with saturated aqueous NaHCO3, dried over Na2SO4, and concentrated. Purification by silica gel chromatography (5% EtOAc in hexanes) provide the title compound (3 g).

Aufarbeitung

  1. customquenched with water
  2. extractionThe product was extracted with CH2Cl2
  3. washthe organics were washed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d88c9ab17aa946a0954bc72cc2376f62
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732480B2

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