Cornforth reagent → HCID 54439755, compound

HRID 1387637Notes

Reaction equation

HRID 1387637 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:17])[CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:19].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9](=[O:17])[C:10]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 54046665HCID 54046665, compound

Product 1

HCID 54439755HCID 54439755, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-methylthiophenyl)-2-(4-pyridyl)ethanol (2.5 g, 10.2 mmol) in CH2Cl2 (150 mL) was added a mixture of celite (4.4 g) and pyridinium dichromate (4.4 g, 20.4 mmol). After stirring for 12 h, the mixture was filtered through celite. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with a solvent gradient of 40-50% EtOAc/Hex to provide the title compound (144 mg, 5.5%): 1H NMR (CDCl3): d 8.88 (br d, 2H); 7.85 (s, 1H); 7.78 (d, 2H); 7.67(d, 1H); 7.56 (d, 1H); 7.44 (t, 1H); 2.55 (s, 3H).

Workup

  1. filtrationthe mixture was filtered through celite
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography
  4. washeluting with a solvent gradient of 40-50% EtOAc/Hex

Sources & evidence

ORD record
ord-80cb77e99eeb434ba4846c32918ad165
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

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