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