Cornforth reagent → HCID 59678349, compound

HRID 251649Notes

Reaction equation

HRID 251649 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>C(Cl)Cl>[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

4

Reactant 2

HCID 2724130Cornforth reagentHCID 67266571HCID 67266571, compound

Product 1

HCID 59678349HCID 59678349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 CH2Cl2 (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-3b2f614656f44c6d8bd15b7880fee752
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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