Methanol → Methyl (2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoate

HRID 705794Notes

Reaction equation

HRID 705794 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])[CH:4]=[N:3]1.OS(O)(=O)=O.[OH-].[Na+].[CH3:19]O>>[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:19])=[O:10])[CH:4]=[N:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1529858(2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acid

Product 1

HCID 21936263Methyl (2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoateYield 71.8%

Procedure

(2E)-3-(1-Methyl-1H-pyrazol-4-yl)-2-propenoic acid (7.5 g, 49.3 mmol) was added to a solution of H2SO4 (1.760 ml, 33.0 mmol) in methanol (40 ml), and the resultant mixture was refluxed for 4 h. It was cooled to room temperature, then poured into ice. The acid was neutralized with aqueous sodium hydroxide and extracted with DCM (80 ml×2). The organic phases were collected and combined, dried over MgSO4, and concentrated. The residue was washed with petroleum ether and concentrated to give the title compound (7 g, 71.8% yield). LCMS: rt=1.13 min, [M+H+]=167

Workup

  1. additionpoured into ice
  2. extractionextracted with DCM (80 ml×2)
  3. customThe organic phases were collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washThe residue was washed with petroleum ether
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-52475a58137749fb97b509c91d3bfedc
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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