Dichloromethane → 5-Tert-butyl-2-p-tolyl-2h-pyrazole-3-carbaldehyde

HRID 2353564Notes

Reaction equation

HRID 2353564 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:17][OH:18])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O>[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[O:18])[N:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 67091382(5-Tert-butyl-2-p-tolyl-2h-pyrazol-3-yl)-methanol

Product 1

HCID 574185555-Tert-butyl-2-p-tolyl-2h-pyrazole-3-carbaldehydeYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a scintillation vial containing (5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-methanol (0.515 g, 2.1 mmol) was added 15 mL DCM followed by the addition of Dess-Martin periodinane (1.1 g, 2.52 mmol). The reaction mixture was allowed to stir at room temperature for 20 minutes and poured into a separatory funnel containing 30 mL water. The layers separated and the aqueous layer extracted twice more with 50 mL DCM. The combined organic layers were washed with Brine, dried over MgSO4 and concentrated under vacuum to afford the crude aldehyde. The crude material was purified by flash chromatography (0-50% EtOAc:Hexanes, silica gel) to yield the desired product as a clear oil (0.5 g, 97%). Expected mass=242. Observed mass=243.

Workup

  1. additionpoured into a separatory funnel
  2. customThe layers separated
  3. extractionthe aqueous layer extracted twice more with 50 mL DCM
  4. washThe combined organic layers were washed with Brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customto afford the crude aldehyde
  8. customThe crude material was purified by flash chromatography (0-50% EtOAc:Hexanes, silica gel)

Sources & evidence

ORD record
ord-c78997c7d35249e4b1c8337b61962859
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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