3-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-ol → 3-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehyde

HRID 2106052Notes

Reaction equation

HRID 2106052 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][CH3:15])([CH3:6])[CH2:3][CH2:4][OH:5].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:6][C:2]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][CH3:15])([CH3:1])[CH2:3][CH:4]=[O:5]

Participants

4

Reactant 2

HCID 578097383-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 578098963-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-3-(2-methoxy-5-fluorophenyl)butan-1-ol (3.30 g) in methylene chloride (40 mL) stirred at room temperature was added pyridinium chlorochromate (4.2 g) portionwise over 5 minutes. The mixture was stirred for 3 hours and then filtered through CELITE® filter aid. The solvent was evaporated in vacuo and the residue was fractionated by chromatography over silica gel (methylene chloride-hexane (1:3 to 1:1 gradient)) to give 3-methyl-3-(2-methoxy-5-fluorophenyl)butyraldehyde an oil (2.5 g, 76%).

Workup

  1. filtrationfiltered through CELITE®
  2. filtrationfilter aid
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-cd2c7cdc310e47c08ccff6cf3df05cce
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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