Water → Methyl 1-t-butyl-pyrazole-4-carboxylate

HRID 2261293Notes

Reaction equation

HRID 2261293 reaction equation
[Na].[CH3:2][O:3][CH:4]([O:12]C)[C:5](=[CH:10]O)[C:6](OC)=O.Cl.[C:15]([NH:19][NH2:20])([CH3:18])([CH3:17])[CH3:16].O>C(O)C>[C:15]([N:19]1[CH:10]=[C:5]([C:4]([O:3][CH3:2])=[O:12])[CH:6]=[N:20]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 81889tert-Butylhydrazine monohydrochlorideHCID 86612677Methyl 2-(dimethoxymethyl)-3-hydroxyacrylate sodium salt

Product 1

HCID 57736385Methyl 1-t-butyl-pyrazole-4-carboxylateYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

8.51 g of methyl 2-(dimethoxymethyl)-3-hydroxyacrylate sodium salt of was suspended in 80 ml of ethanol, and 8.09 g of t-butylhydrazine hydrochloride was then 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 recrystallized from hexane to obtain 5.26 g of methyl 1-t-butyl-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
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-5d76b879761744e08e2d9a99991f36fe
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

Loading…