Acetone → 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic Acid

HRID 1761564Notes

Reaction equation

HRID 1761564 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH2:23][OH:24])[CH:9]=2)=[CH:4][CH:3]=1.CC(C)=[O:27]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][C:23]([OH:27])=[O:24])[CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 14497416HCID 14497416, compound

Product 1

HCID 1888503-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic AcidYield 92%

Procedure

To a solution of the alcohol 2 [(0.92 g, 2.68 millimoles (mM)] in acetone (25 ml) was added a 2N H2Cr2O7 (Jones Reagent) solution (3.02 ml, 6.04 mM) dropwise over a 10 minute time period. After stirring for 1 hour the reaction solution was decanted from the chromium precipitates on the sides of the reaction vessel. The reaction solution was concentrated in vacuo and taken up into ethyl acetate (EtOAc) (100 ml), washed with distilled H2O until the washes were clear, dried (MgSO4), filtered, and concentrated in vacuo. Crystallization from Et2O: hexane afforded 12 (0.88 g, 92%) as an off-white crystalline solid, mp=126°-128° C.

Workup

  1. customwas decanted from the chromium
  2. customprecipitates on the sides of the reaction vessel
  3. concentrationThe reaction solution was concentrated in vacuo
  4. washwashed with distilled H2O until the washes
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customCrystallization from Et2O

Sources & evidence

ORD record
ord-fc8184cc32c6404a972083a34dde419c
Source dataset
uspto-grants-1989_05
Patent number
US04826868

Reaction notes

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