Ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate → 1-(3,5-Dichloro-1-methylpyrazol-4-yl)-2-phenylethanone

HRID 230095Notes

Reaction equation

HRID 230095 reaction equation
[C:1]1([C:7](=[C:13]([C:15]2[C:16]([Cl:22])=[N:17][N:18]([CH3:21])[C:19]=2[Cl:20])[OH:14])C(OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl.O1CCOCC1>[Cl:22][C:16]1[C:15]([C:13](=[O:14])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:19]([Cl:20])[N:18]([CH3:21])[N:17]=1

Participants

4

Reactant 1

HCID 57189495Ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate

Product 1

HCID 221695091-(3,5-Dichloro-1-methylpyrazol-4-yl)-2-phenylethanoneYield 59.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

17 g (50 mmols) of ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate was dissolved in 50 ml of 6 N HCl and 250 ml of 1,4-dioxane, and heated under reflux for 15 hours. The reaction mixture was poured into 500 ml of ice water, and precipitated crystals were taken out through filtration to obtain 8 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethanone as white crystals. m.p.: 94-96° C.

Workup

  1. temperatureunder reflux for 15 hours
  2. customprecipitated crystals
  3. filtrationwere taken out through filtration

Sources & evidence

ORD record
ord-8d2d1c65ea474a0a9efa2c94b2326657
Source dataset
uspto-grants-2009_07
Patent number
US07566683B2

Reaction notes

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