Citric Acid → HCID 178494529, compound

HRID 872880Notes

Reaction equation

HRID 872880 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:8]=[C:7]([C:9]([O:11]CC)=[O:10])[NH:6][N:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[CH3:1][O:2][CH2:3][C:4]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[NH:6][N:5]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178469092HCID 178469092, compound

Product 1

HCID 178494529HCID 178494529, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Ethyl 3-(methoxymethyl)-1H-pyrazole-5-carboxylate (2.44 g, 13.25 mmol) dissolved in methanol (40 ml) and cesium carbonate (8.63 g, 26.5 mmol) dissolved in water (40 ml) were loaded into a flask and stirred overnight at RT under nitrogen atmosphere. Ethyl acetate (100 ml) and water (100 ml) were added and the pH was adjusted to 3 with 10% citric acid. Phases were separated and the water phase was extracted with more ethyl acetate. The combined organic phases were dried with Na2SO4, filtered and evaporated. The product was purified with flash chromatography. Yield 36.5%. 1H-NMR (400 MHz; DMSO-d6): δ 3.25 (s, 3H), 4.40 (s, 2H), 6.67 (s, 1H), 13.16 (bs, 2H).

Workup

  1. customwere loaded into a flask
  2. customPhases were separated
  3. extractionthe water phase was extracted with more ethyl acetate
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-bcb5325b4749427ca088f54af6b1f150
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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