HCID 19982290, compound → HCID 53977640, compound

HRID 1460700Notes

Reaction equation

HRID 1460700 reaction equation
O.[C:2]1([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:10]([CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]/[CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]1([C:42]2[C:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[C:45]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[N:44]([CH2:59][CH2:60][CH2:61]/[CH:62]=[CH:63]/[CH2:64][CH2:65][CH2:66][C:67]([OH:69])=[O:68])[N:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>S(=O)(=O)(O)O.CO>[C:2]1([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:10]([CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH2:68].[C:36]1([C:42]2[C:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[C:45]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[N:44]([CH2:59][CH2:60][CH2:61]/[CH:62]=[CH:63]/[CH2:64][CH2:65][CH2:66][C:67]([OH:69])=[O:68])[N:43]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 2

HCID 19982290HCID 19982290, compoundHCID 67793009HCID 67793009, compound

Product 2

HCID 53977640HCID 53977640, compoundHCID 67793009HCID 67793009, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of (Z) and (E)-9-(3,4,5-triphenyl-1H-pyrazol-1-yl)-5-nonenoic acid (3:1), (850 mg, 1.9 mmol) and concentrated sulfuric acid (2 drops) in methanol (75 mL) was heated at reflux for 1.5 hours. The solvent was evaporated, the residue dissolved in CH2Cl2, washed with water and saturated sodium chloride solution before being dried over sodium sulfate. Evaporation of the solvent left an oil which was chromatographed on a column of silica gel. Elution with a mixture of hexane and ethyl acetate (17:3) containing 1% triethylamine gave methyl 9-(3,4,5-triphenyl-1H-pyrazol-1-yl)-5-nonenoate as a 3:1 ratio of (Z) to (E) geometrical isomers. MS(CI): m/e=465 (MH+).

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in CH2Cl2
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialbefore being dried over sodium sulfate
  6. customEvaporation of the solvent
  7. waitleft an oil which
  8. customwas chromatographed on a column of silica gel
  9. washElution
  10. additionwith a mixture of hexane and ethyl acetate (17:3)
  11. additioncontaining 1% triethylamine

Sources & evidence

ORD record
ord-f64af399062741b29b4d6fab18b3c67a
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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