1-Cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene → Protrifenbute

HRID 1588892Notes

Reaction equation

HRID 1588892 reaction equation
[CH:1]1([C:4]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:5][CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=2)[CH2:3][CH2:2]1>C(O)C.[Ni]>[CH:1]1([CH:4]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 543787091-Cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene

Product 1

HCID 6451141ProtrifenbuteYield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Using a Parr hydrogenation apparatus, a solution of 1.7 grams (0.004 mole) of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl) -1,3-butadiene in 100 mL of absolute ethanol was hydrogenated in the presence of 0.3 gram of Raney nickel (50% in water). Upon completion of the hydrogenation, the reaction mixture was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 10% cyclohexane in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.2 grams of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)butane. The nmr spectrum was consistent with the proposed structure.

Workup

  1. concentrationUpon completion of the hydrogenation, the reaction mixture was concentrated under reduced pressure to a residue
  2. washElution
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52f0e4455db541af8b34a01985583b96
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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