Chloromethyl Methyl Ether → 3-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221663Notes

Reaction equation

HRID 2221663 reaction equation
[OH:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH3:15][O:16][CH2:17]Cl.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:15][O:16][CH2:17][O:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 178519806HCID 178519806, compound

Product 1

HCID 230765133-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehydeYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (1.88 g), chloromethyl methyl ether (0.835 mL), N,N-diisopropylethylamine (2.09 mL) and tetrahydrofuran (30 mL) was stirred at room temperature for 2 hrs. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with diisopropyl ether-hexane to give 3-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde as white crystals (1.34 g, yield 58%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 106-107° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with diisopropyl ether-hexane

Sources & evidence

ORD record
ord-cd474026754942c88a04e9bb6559bb96
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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