Benzyl Chloride → HCID 69157883, compound

HRID 968674Notes

Reaction equation

HRID 968674 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH:26]=[C:25]([OH:27])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:23]1>CN(C=O)C.CCOC(C)=O>[CH2:7]([O:27][C:25]1[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:23][N:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])[CH:26]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 711109ethyl 1-(2-fluorophenyl)-4-hydroxypyrazole-3-carboxylate

Product 1

HCID 69157883HCID 69157883, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

K2CO3 (2.00 g) and benzylchloride (1.2 mL) were added to a solution of ethyl 1-(2-fluorophenyl)-4-hydroxypyrazole-3-carboxylate (2.47 g) in anhydrous DMF (20 mL) at room temperature, and the mixture was stirred overnight. The mixture was diluted with EtOAc and washed with H2O, sat. NaHCO3 and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/19, 1/9, 1/4 and 1/2) to yield 3.09 g of the title compound.

Workup

  1. washwashed with H2O, sat. NaHCO3 and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/19, 1/9, 1/4 and 1/2)

Sources & evidence

ORD record
ord-42a933dae71a4435bb26fc5365c8f0bc
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

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