Water → 1-Ethyl [2-oxo-3-(2-oxo-2-phenylethyl)cyclohexyl]acetate

HRID 12608

Reaktionsgleichung

Reaktionsgleichung von HRID 12608
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[OH2:11].[C:12]([O:15][CH2:16][CH3:17])(=[O:14])[CH3:13]>CN(C)C=O>[O:11]=[C:5]1[CH:10]([CH2:2][C:3](=[O:4])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:9][CH2:8][CH2:7][CH:6]1[CH2:13][C:12]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 8857Ethyl Acetate

Produkt 1

HCID 688589331-Ethyl [2-oxo-3-(2-oxo-2-phenylethyl)cyclohexyl]acetateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Intermediate 2 (667 mg, 2.81 mmol) was dissolved in dimethylformamide (14 ml), 2-bromo-1-phenylethanone (560 mg, 2.81 mmol) was added and the reaction stirred for 24 h at room temperature. Water (5 ml) was added and the reaction allowed to stir for a further 24 h. The mixture was then diluted with ethyl acetate (100 ml) and washed with water. The aqueous fraction was re-extracted three times with ethyl acetate and the combined organic fractions washed three times with water, then dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (10-20% ethyl acetate/hexanes) provided the title compound as a pale yellow oil (428 mg, 50%).

Aufarbeitung

  1. stirringto stir for a further 24 h
  2. washwashed with water
  3. extractionThe aqueous fraction was re-extracted three times with ethyl acetate
  4. washthe combined organic fractions washed three times with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6954c721ef9f486e9691b22e474bc1ae
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728022B2

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