HCID 19982294, compound → HCID 67793900, compound

HRID 1460711Notes

Reaction equation

HRID 1460711 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[O:34])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=[O:37].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH2:34].[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:37])=[O:34])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 19982294HCID 19982294, compoundHCID 131709961Jones' reagent

Product 1

HCID 67793900HCID 67793900, compoundYield 188%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,4,5-triphenyl-1H-pyrazole-1-decanal (2.42 g, 5.4 mmol) in acetone (47 mL maintained at 0° C. was added dropwise 1.75 mL (7 mmol) of 8N Jones reagent. The ice water was removed and the mixture stirred for 48 minutes before being diluted with acetone, filtered through diatomaceous earth and concentrated. The residual oil was chromatographed on a column of silica gel using a mixture of hexane and ethyl acetate (13:7) as eluent to afford 3,4,5-triphenyl-1H-pyrazole-1-decanoic acid hydrate (2.46 g, 81%) as an oil. MS(CI): m/e=467 (MH+).

Workup

  1. customThe ice water was removed
  2. additionbefore being diluted with acetone
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated
  5. customThe residual oil was chromatographed on a column of silica gel using
  6. additiona mixture of hexane and ethyl acetate (13:7) as eluent

Sources & evidence

ORD record
ord-7e69e65632084355b4481de485f53b71
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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