Pyridine → ethyl 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carboxylate

HRID 2221696Notes

Reaction equation

HRID 2221696 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][NH:7][N:6]=1.[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.N1C=CC=CC=1.ClCCl>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH3:15])[N:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 27332672-Methylphenyl boronic acidHCID 178469943HCID 178469943, compound

Product 1

HCID 23076555ethyl 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(methoxymethoxy)-1H-pyrazole-4-carboxylate (1.80 g), 2-methylphenylboronic acid (2.45 g), pyridine (1.46 mL), copper(II) acetate (2.45 g) and dichloromethane (50 mL) was stirred at room temperature for 16 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:9-1:1, v/v) to give ethyl 3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazole-4-carboxylate as a pale-yellow oil (2.39 g, yield 92%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:9-1:1

Sources & evidence

ORD record
ord-ee594c0dff264f2a87ef524063f06274
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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