Pyridine → [2-(Diethoxymethyl)phenyl](2-fluorophenyl)-methanone
Reaction equation
N1C=CC=CC=1.O=[Si]=O.[CH2:10]([O:12][CH:13]([O:29][CH2:30][CH3:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])[OH:21])[CH3:11]>[O-2].[O-2].[O-2].[Cr+6].ClCCl>[CH2:30]([O:29][CH:13]([O:12][CH2:10][CH3:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])=[O:21])[CH3:31]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Under a nitrogen atmosphere, 758 ml of pyridine and 469 g of dicalite were added to 6 l of dry dichloromethane. In one portion 469 g of chromium trioxide were added under vigorous stirring. The resulting mixture was stirred at room temperature for 0.5 h, after which a solution of 238 g of 2-(diethoxymethyl)-α-(2-fluorophenyl)-benzenemethanol in 600 ml dry dichloromethane was added. After stirring at room temperature for 2 h, the mixture was filtered. The filtrate was washed with 3×1 l of 1N sodium hydroxide in water and 1 l of water, dried over magnesium sulphate and evaporated to dryness under reduced pressure to yield 224 g of [2-(diethoxymethyl)phenyl](2-fluorophenyl)-methanone as an oil, M.S. (C.I.) (M/Z) 303 [M+H]+.
Workup
- stirringAfter stirring at room temperature for 2 h
- filtrationthe mixture was filtered
- washThe filtrate was washed with 3×1 l of 1N sodium hydroxide in water and 1 l of water
- dry with materialdried over magnesium sulphate
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-5741b467037840f98475cb04f60cf098
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313139B1
Reaction notes
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