Cornforth reagent → HCID 86587503, compound

HRID 985418Notes

Reaction equation

HRID 985418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[N:10][NH:11][C:12]=1[CH:13]([OH:15])[CH3:14].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[C:13]([C:12]1[NH:11][N:10]=[C:9]([O:16][S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)(=[O:18])=[O:19])[C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86587502HCID 86587502, compound

Product 1

HCID 86587503HCID 86587503, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To toluene-4-sulfonic acid 4-(2-fluorophenyl)-5-(1-hydroxyethyl)-1H-pyrazol-3-yl ester (16.4 g, 43.6 mmol) in dichloromethane (500 ml) was added pyridinium dichromate (19.7 g, 52.3 mmol) and the resulting slurry was stirred at room temperature for 1 h. The mixture was poured directly onto a column of silica gel, and the product was eluted off with ethyl acetate, yielding toluene-4-sulfonic acid 5-acetyl-4-(2-fluorophenyl)-1H-pyrazol-3-yl ester as a yellow solid (8.64 g). 1H NMR (400 MHz, CDCl3) δ 2.16 (3H, s), 2.43 (3H, s), 7.09 (1H, m), 7.22 (3H, m), 7.34 (1H, m), 7.41 (1H, m), 7.65 (2H, d, J=6.8 Hz); MS (ES+) m/e 375 [MH]+.

Workup

  1. additionThe mixture was poured directly onto a column of silica gel
  2. washthe product was eluted off with ethyl acetate

Sources & evidence

ORD record
ord-20adfcaaa53a4953b98431b592acc2ee
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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