Cyclohexyl(4-methoxyphenyl)methanone → HCID 12299666, compound

HRID 1857210Notes

Reaction equation

HRID 1857210 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[S-].[Na+]>CN(C)C=O>[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 345014Cyclohexyl(4-methoxyphenyl)methanoneHCID 4378561Sodium methanethiolate

Product 1

HCID 12299666HCID 12299666, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Cyclohexylcarbonyl-1-methoxybenzene (517 mg) obtained in Example 141 was dissolved in N,N-dimethylformamide (20 ml), sodium thiomethoxide (538 mg) was added, and the admixture was refluxed with heat for 1 hour under argon. The reaction mixture was partitioned between water and ethyl acetate, and the ethyl acetate layer was washed with brine and then dried with anhydrous sodium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/acetone to obtain 487 mg of the title compound (yield: 93%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 1 hour under argon
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customAfter removing the solvent
  7. distillationby reduced-pressure distillation
  8. customthe resulting residue was purified by chromatography on silica gel eluting with hexane/acetone

Sources & evidence

ORD record
ord-f0b0c45e30564a79a061673e234280ef
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…