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Potassium Carbonate → ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate

HRID 79308
Notes
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Reaction equation

HRID 79308 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:1]2[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]2)=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 44558860ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylateYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To ethyl 1H-pyrazole-4-carboxylate (5.01 g, 35.7 mmol) in DMF (60 mL) was added 1-(chloromethyl)-4-methoxybenzene (6.16 g, 39.3 mmol) and K2CO3 (7.41 g, 53.6 mmol). The reaction mixture was stirred for 16 hours and concentrated under reduced pressure to remove DMF. The residue was diluted with EtOAc (100 mL), washed with H2O (30 mL) and brine (20 mL), dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/hexanes 1:5) provided the desired product (8.31 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove DMF
  3. additionThe residue was diluted with EtOAc (100 mL)
  4. washwashed with H2O (30 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a325198d1ef4226adffc2dd3c2b197a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841455B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes