(4E)-3-(4-Chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol → (4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexenal
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8](/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[CH2:9][CH:10]=[O:11])=[CH:6][CH:7]=1Participants
4
Procedure
To a stirred solution of (4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol (0.332 g, 0.80 mmol) in methylene chloride (20 ml) at room temperature under nitrogen was added pyridinium chlorochromate (PCC; 0.268 g, 1.24 mmol), and the resulting mixture was stirred for four hours. The reaction mixture was diluted with methylene chloride, washed sequentially with 10% hydrochloric acid, water, saturated sodium bicarbonate and water, and dried over anhydrous sodium sulfate. Concentration in vacuo afforded the title compound as a brown oil (0.324 g) which was characterized by 1HNMR, 19FNMR and mass spectral analysis, and used without further purification.
Workup
- washwashed sequentially with 10% hydrochloric acid, water, saturated sodium bicarbonate and water
- dry with materialdried over anhydrous sodium sulfate
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-cf9e8fb537cd4d02b6185a8f562618e8
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506800B2
Reaction notes
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