Trityl chloride → 5-Methyl-1-trityl-1H-pyrazole-3-carbaldehyde

HRID 493720Notes

Reaction equation

HRID 493720 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.C(N(CC)CC)C.Cl[C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([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(#N)C>[CH3:1][C:2]1[N:6]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 45602443-methyl-1H-pyrazole-5-carbaldehyde

Product 1

HCID 231309495-Methyl-1-trityl-1H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-methyl-1H-pyrazole-3-carbaldehyde (Werner A. et al., Tetrahedron, 51, 4779 (1995): 1.1 g) in acetonitrile (20 mL), triethylamine (1.5 mL) and chlorotriphenylmethane (3.1 g) were added and mixed for 12 hours. The reaction solution was concentrated, and the residue was dissolved in chloroform. This solution was washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with a silica gel column to give the title compound (1.9 g) as a colorless solid.

Workup

  1. additionmixed for 12 hours
  2. concentrationThe reaction solution was concentrated
  3. dissolutionthe residue was dissolved in chloroform
  4. washThis solution was washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified with a silica gel column

Sources & evidence

ORD record
ord-c0df0a26c733414cb6ce24a454ee818a
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

Loading…