Sodium Carbonate → HCID 57572363, Verbindung

HRID 907517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907517
[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[N:11][OH:12])[C:7]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CCCCCC>[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[N:11][OH:12])[C:7]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 73064693HCID 73064693, Verbindung

Produkt 1

HCID 57572363HCID 57572363, VerbindungAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 27 mg 3-cyclopentyl-2-(3-methoxyphenyl)-2-cyclopenten-1-one oxime (Example 7) in 5 ml dichloromethane at −78° C., was added 0.5 ml 1.0 M boron tribromide in hexane dropwise under inert atmosphere. The reaction mixture was stirred for 2 hours while being allowed to gradually warm to room temperature. Then the reaction mixture was poured into saturated aqueous sodium carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=1:1) to yield 12 mg of 3-cyclopentyl-2-(3-hydroxyphenyl)-2-cyclopenten-1-one oxime as a solid. mp=207-209° C.; 1H NMR (CDCl3, 300 MHz): δ 7.26-7.21 (m, 2H), 6.79-6.70 (m, 3H), 2.93 (m, 1H), 2.80 (m, 2H), 2.61 (m, 2H), 1.70 (m, 4H), 1.54 (m, 4H); APCI MS: m/z 258.1 (M+1).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (silica gel, hexane/ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ff4b4ee53eb846d9bfc5a5129415d679
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013187B2

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