Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate → Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-formyl-pyridine-5-carboxylate

HRID 324791Notes

Reaction equation

HRID 324791 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]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:17]([CH:35]([CH3:37])[CH3:36])[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]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:17]([CH:35]([CH3:36])[CH3:37])[N:16]=1)([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 10291957Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 22005047Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-formyl-pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14.18 g (0.139 mol) of neutral Al2O3 and 29.96 g (0.13 mol) of pyridinium chlorochromate (PCC) are added to a solution of 25.0 g (0.0695 mol) of the compound from Example IX in 500 ml CH2Cl2 and the mixture is stirred for 1 h at room temperature. It is drawn off by suction over silica gel and subsequently washed with CH2Cl2, and the filtrate is concentrated in a vacuum, whereby the product precipitates out.

Workup

  1. washsubsequently washed with CH2Cl2
  2. concentrationthe filtrate is concentrated in a vacuum, whereby the product
  3. customprecipitates out

Sources & evidence

ORD record
ord-c603be94b9a84f77b5e4d8f1a025112d
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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