Cornforth reagent → 6-[2-(1H-Imidazol-1-yl)-3-methyl-1H-indol-1-yl]hexanoic acid

HRID 1719399Notes

Reaction equation

HRID 1719399 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[C:9]1[N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:24].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[C:9]1[N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)([OH:24])=[O:2]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 202681931-(5-Formylpentyl)-2-(1-imidazolyl)-3-methylindole

Product 1

HCID 132808416-[2-(1H-Imidazol-1-yl)-3-methyl-1H-indol-1-yl]hexanoic acid

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1-(5-Formylpentyl)-3-methyl-2-(1-imidazolyl)indole (115 mg) is dissolved in dimethylformamide (1.0 ml) and pyridinium dichromate (300 mg) added all at once. The mixture is stirred overnight at room temperature, then diluted with chloroform, and the combined filtrate is extracted with 0.1N aqueous sodium hydroxide (2 ml). The aqueous extract is acidified to about pH 5.5-6.0 and extracted with chloroform. The chloroform extract is dried and concentrated in vacuo. Purification by chromatography on silica gel yields 1-(5-carboxypentyl)-2-(1-imidazolyl)-3-methylindole.

Workup

  1. extractionthe combined filtrate is extracted with 0.1N aqueous sodium hydroxide (2 ml)
  2. extractionThe aqueous extract
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. customis dried
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-c386513d184b46b798507e8eccc41780
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

Loading…