Hydrogen Peroxide → HCID 10643322, compound

HRID 1780852Notes

Reaction equation

HRID 1780852 reaction equation
[CH3:1][O:2][C:3]1([O:25][CH3:26])[CH2:8][CH2:7][C:6]([C:23]#[N:24])([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-:28].[K+].[K+].OO>CO.O.[Cl-].[Na+].O>[CH3:26][O:25][C:3]1([O:2][CH3:1])[CH2:8][CH2:7][C:6]([C:23]([NH2:24])=[O:28])([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 10832317HCID 10832317, compound

Product 1

HCID 10643322HCID 10643322, compoundYield 15.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal (0.34 g, 0.95 mmol) and powdered potassium carbonate (0.7 g, 5.1 mmol) in methanol (20 mL) and water (4 mL) at 0° C. was treated with hydrogen peroxide (30% solution, 2.55 mL). The mixture was allowed to warm to room temperature and, after seven days, brine was added and the mixture was extracted with methylene chloride. The organic extract was washed twice with brine, dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography provided the amide (0.055 g, 15%) along with recovered starting material (0.25 g).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. extractionThe organic extract
  3. washwas washed twice with brine
  4. dry with materialdried (potassium carbonate)
  5. customthe solvent was removed in vacuo
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-2a7de99c6602414f8419168f4a9d26b2
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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