Chloromethyl Methyl Ether → 4-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylate

HRID 2221694Notes

Reaction equation

HRID 2221694 reaction equation
[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1.[CH3:19][O:20][CH2:21]Cl.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:19][O:20][CH2:21][O:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[N:3]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 178469862HCID 178469862, compound

Product 1

HCID 692165114-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylateYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-ethyl 1-tert-butyl 3-hydroxy-1H-pyrazole-1,4-dicarboxylate (30.75 g), chloromethyl methyl ether (4.56 mL), N,N-diisopropylethylamine (11.9 mL) and tetrahydrofuran (150 mL) was stirred at room temperature for 2 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, 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 (1:9-1:2, v/v) to give 4-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylate as a pale-yellow oil (3.52 g, yield 20%).

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 (1:9-1:2

Sources & evidence

ORD record
ord-a9a9cbdad13f4413aa568e0beb9cc5e3
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…