Ethanol → Ethyl 3-methyl-1H-pyrazole-1-acetate

HRID 1777748Notes

Reaction equation

HRID 1777748 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]([OH:10])=[O:9])[N:3]=1.OS(O)(=O)=O.[CH3:16][CH2:17]O>C(Cl)Cl>[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]([O:10][CH2:16][CH3:17])=[O:9])[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 50123292-(3-methyl-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 4578874Ethyl 3-methyl-1H-pyrazole-1-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of (3-methyl-1H-pyrazol-1-yl)acetic acid (200 mg) and H2SO4 (0.1 mL) in EtOH (2 mL) was stirred at 80° C. for 4 h. After cooling down, the reaction mixture was diluted with DCM and washed with sat. Na2CO3, water and brine. The aq. layers were extracted with DCM, the combined org. layers were dried (MgSO4), filtered off and evaporated in vacuo to afford ethyl 2-(3-methyl-1H-pyrazol-1-yl)acetate (101 mg, colourless liquid). LC-MS (B): tR=0.57 min; [M+H]+: 169.01.

Workup

  1. temperatureAfter cooling down
  2. washwashed with sat. Na2CO3, water and brine
  3. extractionThe aq. layers were extracted with DCM
  4. dry with materiallayers were dried (MgSO4)
  5. filtrationfiltered off
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e6189fb7faca414499d065a297922990
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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