Triacetoxyperiodinane → HCID 58360612, compound

HRID 2194849Notes

Reaction equation

HRID 2194849 reaction equation
[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:6]=[C:5]([CH2:18][OH:19])[CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)[N:6]=[C:5]([CH:18]=[O:19])[CH:4]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58360630HCID 58360630, compound

Product 1

HCID 58360612HCID 58360612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 mL round-bottomed flask was charged with (5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methanol 73 (4.60 g, 16.9 mmol) and 50 mL of CH2Cl2. To this solution was added Dess-Martin periodinane (8.96 g, 21.1 mmol) and the mixture was stirred at room temperature for 1.5 h. The reaction mixture was quenched with saturated aqueous Na2S2O3, extracted with CH2Cl2, dried, and concentrated. Purification by via column chromatography on silica gel (0% to 20% EtOAc in hexanes) to give 5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde 74.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous Na2S2O3
  2. extractionextracted with CH2Cl2
  3. customdried
  4. concentrationconcentrated
  5. customPurification by via column chromatography on silica gel (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-103fdbead8c1483b9b40d773777a0f76
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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