Trityl chloride → Ethyl 1-tritylpyrazole-4-carboxylate

HRID 992682Notes

Reaction equation

HRID 992682 reaction equation
CC(C)([O-])C.[K+].[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:27]([O:29][C:30]([C:32]1[CH:33]=[N:34][NH:35][CH:36]=1)=[O:31])[CH3:28].O.C(OCC)(=O)C>CN(C=O)C>[CH2:27]([O:29][C:30]([C:32]1[CH:33]=[N:34][N:35]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:36]=1)=[O:31])[CH3:28]

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 22728543Water ethylacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10523968Ethyl 1-tritylpyrazole-4-carboxylateYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under N2 atmosphere, potassium tert-butoxide (9.60 g, 85.5 m mol) and trityl chloride (21.9 g, 78.5 m mol) were added successively to a solution of 4-(ethoxycarbonyl)pyrazole (10.0 g, 71.3 m mol) in DMF (100 ml) at 0° C. After stirred for 1 hour, the mixture was poured into water/ethyl acetate. The aqueous layer was separated, and the organic layer was washed with water, brine and dried over magnesium sulfate. After evaporation of the solvent, the resulting precipitate was recrystallized from ethyl acetate to afford 4-ethoxycarbonyl-1-(trityl)pyrazole (21.7 g).

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe resulting precipitate was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4f0cfd2035d048d49bcc4289b5b6845b
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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