4-(5-Fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentan-1-ol → 4-(5-Fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentanal
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([C:8]([CH3:22])([CH3:21])[CH2:9][C:10]([O:17][CH2:18][O:19][CH3:20])([C:13]([F:16])([F:15])[F:14])[CH2:11][OH:12])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([C:8]([CH3:21])([CH3:22])[CH2:9][C:10]([O:17][CH2:18][O:19][CH3:20])([C:13]([F:16])([F:15])[F:14])[CH:11]=[O:12])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2.77 g (7.82 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentan-1-ol in 50 mL of dichloromethane was added 3.8 g (17.63 mmol) of pyridinium chlorochromate. After 3 days, the reaction was diluted with 100 mL of hexanes and filtered through a pad of silica gel in a 150 mL funnel, eluting with EtOAc-hexanes (1:9). Concentration in vacuo afforded 2.56 g (93%) of 4-(5-fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentanal as a clear oil which was used without further purification.