2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethyl-5-methoxyiminomethyl-pyridine → 2,6-Diisopropyl-4-(4-fluorophenyl)-5-methoxyiminomethylpyridine-3-carbaldehyde

HRID 2081270Notes

Reaction equation

HRID 2081270 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH:12]([C:15]1[C:20]([CH2:21][OH:22])=[C:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:18]([CH:30]=[N:31][O:32][CH3:33])=[C:17]([CH:34]([CH3:36])[CH3:35])[N:16]=1)([CH3:14])[CH3:13]>C(Cl)Cl>[CH:12]([C:15]1[C:20]([CH:21]=[O:22])=[C:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:18]([CH:30]=[N:31][O:32][CH3:33])=[C:17]([CH:34]([CH3:36])[CH3:35])[N:16]=1)([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 544628792,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethyl-5-methoxyiminomethyl-pyridineHCID 178418287HCID 178418287, compound

Product 1

HCID 539806372,6-Diisopropyl-4-(4-fluorophenyl)-5-methoxyiminomethylpyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.62 g (6.2 mmol) of neutral alumina and 1.3 g (6.1 mmol) of pyridinium chlorochromate are added to a solution of 1.05 g (3.05 mmol) of the compound from Example 2 in 50 ml of methylene chloride and the mixture is stirred at room temperature for 1 hour. It is filtered through kieselguhr and then washed with 200 ml of methylene chloride. The methylene chloride phase is concentrated in vacuo and the residue is chromatographed on a column (100 g of silica gel, 70-230 mesh, diameter 3.5 cm) using ethyl acetate/petroleum ether 1:9.

Workup

  1. filtrationIt is filtered through kieselguhr
  2. washwashed with 200 ml of methylene chloride
  3. concentrationThe methylene chloride phase is concentrated in vacuo
  4. customthe residue is chromatographed on a column (100 g of silica gel, 70-230 mesh, diameter 3.5 cm)

Sources & evidence

ORD record
ord-85e9cfc30e294ef1ba562ed81076660f
Source dataset
uspto-grants-1993_02
Patent number
US05183897

Reaction notes

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