Sodium Hydroxide → HCID 9951549, compound

HRID 1087091Notes

Reaction equation

HRID 1087091 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][N:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:12]1([C:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][N:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9930281HCID 9930281, compound

Product 1

HCID 9951549HCID 9951549, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3,4-diphenyl-1H-pyrrole-1-nonanoate (2.50g, 6.4mmol), 5N sodium hydroxide solution (3.86mL, 19mmol) and methanol (50mL) was heated on a steam bath. After 30 minutes, the solvent was evaporated, the residue diluted with 1N HC1 solution and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate, concentrated in vacuo and the residual oil chromatographed on a column of silica gel. Elution with a mixture of diethyl ether and hexanes (3:2) gave 3,4-diphenyl-1H-pyrrole-1-nonanoic acid (2.20g, 91%) as an oil.

Workup

  1. temperaturewas heated on a steam bath
  2. customthe solvent was evaporated
  3. additionthe residue diluted with 1N HC1 solution
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residual oil chromatographed on a column of silica gel
  8. washElution
  9. additionwith a mixture of diethyl ether and hexanes (3:2)

Sources & evidence

ORD record
ord-5aa0720ba3114e34898bb50b0db68062
Source dataset
uspto-grants-1991_07
Patent number
US05034409

Reaction notes

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