Triacetoxyperiodinane → 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde

HRID 2194844Notes

Reaction equation

HRID 2194844 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[N:10]2)=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[N:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 44819037{1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}-methanol

Product 1

HCID 574169821-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round-bottomed flask was charged with (1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methanol 64 (0.703 g, 2.90 mmol) and 10 mL CH2Cl2. To this solution was added Dess-Martin periodinane (1.60 g, 3.77 mmol). After stirring at room temperature for 30 min, the reaction was quenched with saturated aqueous sodium thiosulfate. The layers were separated and the organics were dried and concentrated. The concentrate was passed through a short pad of silica gel rinsing with 7:1 hexanes/EtOAc to give 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde 65.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium thiosulfate
  2. customThe layers were separated
  3. customthe organics were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93c130e6b4f146dfa55ac0b0ce0035c5
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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