4-(5-Fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentan-1-ol → 4-(5-Fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentanal

HRID 916013Notes

Reaction equation

HRID 916013 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]=1

Participants

4

Reactant 2

HCID 589599234-(5-Fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 589600374-(5-Fluoro-2-methoxyphenyl)-2-methoxymethoxy-4-methyl-2-trifluoromethylpentanalYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. filtrationfiltered through a pad of silica gel in a 150 mL funnel
  2. washeluting with EtOAc-hexanes (1:9)
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a43e55ea90dc4d159713e2f4d4b5f15c
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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