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

HRID 12608

Reaction equation

HRID 12608 reaction equation
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]

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 8857Ethyl Acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6954c721ef9f486e9691b22e474bc1ae
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Linked notes

Loading…