Water → methyl 1-cyclohexyl-1H-pyrazole-4-carboxylate

HRID 2261315Notes

Reaction equation

HRID 2261315 reaction equation
[Na].[CH3:2][O:3][CH:4]([O:12]C)[C:5](=[CH:10]O)[C:6](OC)=O.Cl.[CH:15]1([NH:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.O>C(O)C>[CH:15]1([N:21]2[CH:10]=[C:5]([C:4]([O:3][CH3:2])=[O:12])[CH:6]=[N:22]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 207836Cyclohexylhydrazine hydrochlorideHCID 86612677Methyl 2-(dimethoxymethyl)-3-hydroxyacrylate sodium salt

Product 1

HCID 57736384methyl 1-cyclohexyl-1H-pyrazole-4-carboxylateYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

3.96 g of methyl 2-(dimethoxymethyl)-3-hydroxyacrylate sodium salt was suspended in 40 ml of ethanol, and 3.13 g of cyclohexylhydrazine hydrochloride was added. The mixture was stirred at 60° C. for 4 hours and then cooled to room temperature. After 50 ml of water was added, the reaction mixture was concentrated to 50 ml under reduced pressure. The concentrated solution was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.01 g of methyl 1-cyclohexyl-1H-pyrazole-4-carboxylate.

Workup

  1. temperaturecooled to room temperature
  2. concentrationthe reaction mixture was concentrated to 50 ml under reduced pressure
  3. extractionThe concentrated solution was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b249cb44a6e04f6f9428d0972980fcdb
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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