Potassium Hydroxide → HCID 54486159, compound

HRID 1636743Notes

Reaction equation

HRID 1636743 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH:14]=[CH:15][CH2:16][N:17]([CH:24]3[CH2:26][CH2:25]3)C(=O)C(F)(F)F)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[K+]>CO.O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH:14]=[CH:15][CH2:16][NH:17][CH:24]3[CH2:26][CH2:25]3)=[CH:10][CH:9]=2)=[O:7])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54298023HCID 54298023, compound

Product 1

HCID 54486159HCID 54486159, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.5 g of N-[4-[4-(4-bromo-benzoyl)-phenoxy]-but-2-enyl]-N-cyclopropyl-2,2,2-trifluoroacetamide in 150 ml of methanol and 50 ml of tetrahydrofuran is treated with 5 ml of 20% aqueous potassium hydroxide solution while cooling with ice. The mixture is brought to room temperature and stirred for one hour, concentrated under reduced pressure and the residue is treated with 100 ml of water. The phases are separated and the inorganic phase is extracted with methylene chloride. The organic extracts are washed with saturated sodium chloride solution, dried and evaporated. After purification of the residue over silica gel with ethyl acetate-hexane-triethylamine (50/49/1) there are obtained 7.0 g of (4-bromo-phenyl)-[4-(4-cyclopropylamino-but-2-enyloxy)-phenyl]-methanone, MS: m/e 386 (M+H+, 1Br),

Workup

  1. temperaturewhile cooling with ice
  2. customis brought to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionthe residue is treated with 100 ml of water
  5. customThe phases are separated
  6. extractionthe inorganic phase is extracted with methylene chloride
  7. washThe organic extracts are washed with saturated sodium chloride solution
  8. customdried
  9. customevaporated
  10. customAfter purification of the residue over silica gel with ethyl acetate-hexane-triethylamine (50/49/1) there

Sources & evidence

ORD record
ord-c864a6cc45d647ecb86caa1f83610582
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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