Cornforth reagent → HCID 59678349, compound

HRID 1392683Notes

Reaction equation

HRID 1392683 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH2:19][CH3:20])=[C:13]([O:22][CH:23]([CH3:25])[CH3:24])[CH:12]=1)[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[CH:15][C:14]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[C:13]([O:22][CH:23]([CH3:25])[CH3:24])[CH:12]=1)[CH3:2]

Participants

3

Reactant 2

HCID 2724130Cornforth reagentHCID 67266571HCID 67266571, compound

Product 1

HCID 59678349HCID 59678349, compound

Procedure

A mixture of 1-[6-(2,6-diethyl-phenyl)-4-isopropoxy-pyridin-3-yl]-butan-1-ol (482 mg, 1.41 mmol, prepared analogously to Example 16) and pyridinium dichromate (1.0 g, 2.82 mmol) in CH2CH2 (50 mL) is stirred at room temperature overnight. The mixture is washed with brine, dried and concentrated. The residue is chromatographed on silica gel to give 360 mg of 1-[6-(2,6-diethyl-phenyl)-4-isopropoxy-pyridin-3-yl]-butan-1-one.

Workup

  1. washThe mixture is washed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-53cff43b3a4d46deb6637cd2004830d8
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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