Potassium Hydroxide → (E)-1-cyclopropyl-1-[4-(difluoromethoxy)phenyl]-N-[(2-methyl-3-phenylphenyl)methoxy]methanimine

HRID 1388948Notes

Reaction equation

HRID 1388948 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[CH:13]2[CH2:15][CH2:14]2)=[N:11]/[OH:12])=[CH:6][CH:5]=1.Cl[CH2:18][C:19]1[C:20]([CH3:31])=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1.[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:31][C:20]1[C:19]([CH2:18][O:12]/[N:11]=[C:10](/[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:16])[F:1])=[CH:9][CH:8]=2)\[CH:13]2[CH2:14][CH2:15]2)=[CH:24][CH:23]=[CH:22][C:21]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 132825193-(Chloromethyl)-2-methyl-1,1'-biphenylHCID 20469188(NE)-N-[cyclopropyl-[4-(difluoromethoxy)phenyl]methylidene]hydroxylamine

Product 1

HCID 88714563(E)-1-cyclopropyl-1-[4-(difluoromethoxy)phenyl]-N-[(2-methyl-3-phenylphenyl)methoxy]methanimineYield 96.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a dry argon atmosphere a solution of 1.0 g (0.0044 mole) of (E)-(4-difluoromethoxyphenyl)(cyclopropyl)methanone oxime in 50 ml of dry tetrahydrofuran was added to a stirred solution of 0.95 g (0.0044 mole) of 3-chloromethyl-2-methyl [1,1'-biphenyl], 0.29 g (0.0044 mole) of powdered potassium hydroxide, and 0.14 g (0.00044 mole) of tetrabutylammonium bromide in 45 ml of dry tetrahydrofuran. The reaction mixture was stirred at room temperature for approximately 18 hours then evaporated under reduced pressure to give a liquid. The liquid was diluted with methylene chloride, and the mixture washed with water. The aqueous wash was extracted with methylene chloride. The organic phases were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give an oil. The oil was subjected to column chromatography on silica gel, eluting with toluene to give 1.73 g of (E)-(4-difluoromethoxyphenyl)(cyclopropyl)methanone O-[(2-methyl[1,1'-biphenyl]-3-yl)methyl]oxime as an oil.

Workup

  1. customthen evaporated under reduced pressure
  2. customto give a liquid
  3. washthe mixture washed with water
  4. washThe aqueous wash
  5. extractionwas extracted with methylene chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure
  9. customto give an oil
  10. washeluting with toluene

Sources & evidence

ORD record
ord-5a8159cd7c9d4c4e9cad1ad43c116d4a
Source dataset
uspto-grants-1984_02
Patent number
US04434182

Reaction notes

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