Water → HCID 13632725, compound

HRID 1984203Notes

Reaction equation

HRID 1984203 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:16](OCC)(=[O:18])[CH3:17].O>C1C=CC=CC=1>[C:16]([CH:9]1[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11][C:10]1=[O:13])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 786054-Phenylcyclohexanone

Product 1

HCID 13632725HCID 13632725, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-phenylcyclohexanone (10 mmol, Lancaster) in benzene (5 ml) is added dropwise to a suspension of NaH (20 mmol) in absolute ethyl acetate (20 mmol) and the reaction mixture is stirred after complete evolution of the gas for 3 h at 40° C. Then it is mixed with water, the reaction mixture is extracted three times with ether, the combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulphate and the solvent is removed in a vacuum. After column chromatography purification on silica gel with hexane/EtOAc 15:1 a clean product is obtained. tR 2.14; MS (pos. Ion.) m/z 217.26 [M+H]+. (J. Med. Chem. 1989, 32(2), 351-357).

Workup

  1. extractionthe reaction mixture is extracted three times with ether
  2. washthe combined organic phases are washed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in a vacuum
  5. customAfter column chromatography purification on silica gel with hexane/EtOAc 15:1 a clean product
  6. customis obtained

Sources & evidence

ORD record
ord-36e18e4451a347cca502560d371ba7c5
Source dataset
uspto-grants-2009_06
Patent number
US07544691B2

Reaction notes

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