Cornforth reagent → HCID 54439755, compound

HRID 479770Notes

Reaction equation

HRID 479770 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-61fdbf4799df4da5adc5b36a585b6a8c
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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