Boron trifluoride etherate → HCID 12094930, Verbindung

HRID 1767763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767763
[C:1]12([C:7]3[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=3)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:6][CH:5]1[CH2:4][CH2:3][CH2:2]2.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][CH:1]1[C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 12094929HCID 12094929, Verbindung

Produkt 1

HCID 12094930HCID 12094930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4 g (17.2 mmol) of ethyl 3-(6-oxabicyclo[3.1.0]hex-1-yl)benzoate (6) and 50 ml of methylene chloride are introduced into a round-bottomed flask. The mixture is cooled to 0° C. and then 2.2 ml (17.2 mmol) of BF3.Et2O are added dropwise. The reaction mixture is stirred at 0° C. for 1 hour and then 25 ml of a saturated aqueous sodium bicarbonate solution are added. The mixture is separated by settling and the aqueous phase extracted with methylene chloride. The combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 80/20). The title product is obtained in the form of a pale yellow oil (3.4 g).

Aufarbeitung

  1. customThe mixture is separated
  2. extractionthe aqueous phase extracted with methylene chloride
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-07b1699948074c4a86098a699d9adef7
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235568B2

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