Methanol → HCID 178469943, compound

HRID 2221695Notes

Reaction equation

HRID 2221695 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][N:7](C(OC(C)(C)C)=O)[N:6]=1.O.[OH-].[Li+].O1CCCC1.CO>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][NH:7][N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 692165114-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylate

Product 1

HCID 178469943HCID 178469943, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylate (3.52 g), lithium hydroxide monohydrate (1.47 g), tetrahydrofuran (60 mL), methanol (30 mL) and water (30 mL) was stirred at room temperature for hrs. Water was added to 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 (1:9-4:1, v/v) to give ethyl 3-(methoxymethoxy)-1H-pyrazole-4-carboxylate as a colorless solid (1.80 g, yield 77%).

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 (1:9-4:1

Sources & evidence

ORD record
ord-433cb0bc2097432e96a4e66cc8802922
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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