Trityl chloride → Ethyl 1-tritylpyrazole-4-carboxylate

HRID 746317Notes

Reaction equation

HRID 746317 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[C:11](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]([N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 10523968Ethyl 1-tritylpyrazole-4-carboxylateYield 115.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.78 g of ethyl pyrazole-4-carboxylate was dissolved in 15 ml of methylene chloride and 1.56 g of trityl chloride and 0.86 ml of triethylamine were added thereto and then the resulting mixture was stirred for 1.5 hours at room temperature. The reaction mixture was washed with 10% aqueous solution of citric acid and SSC and then dried with sodium sulfate. The solvent was distilled off to give 2.45 g of ethyl 1-tritylpyrazole-4-carboxylate as an oil.

Workup

  1. washThe reaction mixture was washed with 10% aqueous solution of citric acid and SSC
  2. dry with materialdried with sodium sulfate
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-83e338035d2f440b8225a6ffe94e7d7d
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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