Pyridine → (3,5-Difluorophenyl)(thiazol-2-yl)methanone

HRID 741806Notes

Reaction equation

HRID 741806 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:9]=[C:10]([CH:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[OH:16])[CH:11]=[C:12]([F:14])[CH:13]=1>C(Cl)Cl>[F:7][C:8]1[CH:9]=[C:10]([C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)=[O:16])[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 194269623,5-Difluoro-alpha-(thiazol-2-yl)benzenemethanol

Product 1

HCID 19426944(3,5-Difluorophenyl)(thiazol-2-yl)methanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of CrO3 (1.1 g, 11 mmol) in CH2Cl2 at r.t. was added pyridine (1.8 mL, 22 mmol) and the resulting mixture was stirred for 20 min.. The alcohol from Step 1 in CH2Cl2 was added and the resulting mixture was stirred for 16 h. Then ET2O was added and the resulting mixture was filtered through silica gel and washed with Et2O. After evaporation the residue was chromatographed on silica gel eluting with 7:3 mixture of hexane:EtOAc to give 1.66 g (90%) of the title compound.

Workup

  1. stirringthe resulting mixture was stirred for 16 h
  2. additionThen ET2O was added
  3. filtrationthe resulting mixture was filtered through silica gel
  4. washwashed with Et2O
  5. customAfter evaporation the residue
  6. customwas chromatographed on silica gel eluting with 7:3 mixture of hexane

Sources & evidence

ORD record
ord-768d9f1bfd10421f92c5fd709e071b5b
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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