3,5-Dihydroxymethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine → 2,6-Diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarbaldehyde

HRID 1681623Notes

Reaction equation

HRID 1681623 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C:14]1[C:15]([CH:32]([CH3:34])[CH3:33])=[N:16][C:17]([CH:29]([CH3:31])[CH3:30])=[C:18]([CH2:27][OH:28])[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1>C(Cl)Cl>[CH:32]([C:15]1[C:14]([CH:13]=[O:12])=[C:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:18]([CH:27]=[O:28])=[C:17]([CH:29]([CH3:31])[CH3:30])[N:16]=1)([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 159242263,5-Dihydroxymethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridineHCID 178418287HCID 178418287, compound

Product 1

HCID 159242272,6-Diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.3 g (48 mmol) of pyridinium chlorochromate and 4.9 g (48 mmol) of neutral alumina are added to a solution of 3.8 g (12 mmol) of the compound from Example 4 in 100 ml of methylene chloride p.a. and the mixture is stirred for 1 h at room temperature. The mixture is filtered over kieselgur with suction and washed with 300 ml of methylene chloride. The methylene chloride phase is concentrated in vacuo and the residue is chromatographed on a column (150 g of silica gel 70-230 mesh, φ 3.5 cm, using ethyl acetate/petroleum ether 2:8).

Workup

  1. filtrationThe mixture is filtered over kieselgur with suction
  2. washwashed with 300 ml of methylene chloride
  3. concentrationThe methylene chloride phase is concentrated in vacuo
  4. customthe residue is chromatographed on a column (150 g of silica gel 70-230 mesh, φ 3.5 cm, using ethyl acetate/petroleum ether 2:8)

Sources & evidence

ORD record
ord-b58bba6d517642f3a198167498f119d8
Source dataset
uspto-grants-1992_12
Patent number
US05173495

Reaction notes

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