Sodium Acetate → HCID 90029515, compound

HRID 1488214Notes

Reaction equation

HRID 1488214 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([CH2:14][OH:15])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.CC([O-])=O.[Na+]>ClCCl>[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([CH:14]=[O:15])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2724130Cornforth reagentHCID 90029703HCID 90029703, compound2×

Product 1

HCID 90029515HCID 90029515, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-benzyl-4-methyl-1H-pyrazol-3-yl)methanol (compound 268.2, 3 g, 14.8 mmol) in dichloromethane (100 mL) was added PDC (11.3 g, 30.1 mmol), molecular sieves (3 g) and NaOAc (300 mg) were added to the reaction mixture. The reaction mixture was stirred for 4 h at room temperature. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1/10) as the eluent to yield 1 g (34%) of the title compound as a colorless oil.

Workup

  1. additionwere added to the reaction mixture
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1/10) as the eluent

Sources & evidence

ORD record
ord-6ad90c0235444c9984e1a5df83c78768
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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