Cornforth reagent → HCID 15591370, compound

HRID 1633147Notes

Reaction equation

HRID 1633147 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[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CCOC(C)=O.CCCCCC>CN(C=O)C.CCOCC.CCOCC.C(OCC)(=O)C>[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[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([OH:25])=[O:2]

Participants

7

Reactant 3

HCID 2724130Cornforth reagentHCID 13362113HCID 13362113, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 15591370HCID 15591370, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

1-(5-Formylpentyl)-3-methyl-2-(3-pyridyl)indole (127 mg) is dissolved in DMF (0.66 ml) and pyridinium dichromate (298 mg) added all at once. The mixture is stirred overnight at room temperature then diluted with ether:ethyl acetate (25 ml, 4:1) and filtered. The solid is washed with hot chloroform and the combined filtrates concentrated in vacuo to yield a dark brown gum which is slurried in ether:ethyl acetate (4:1) and extracted with 0.1 N aqueous sodium hydroxide (2 ml). The aqueous extract is acidified to pH 5.5-6.0 and extracted with chloroform. The chloroform extract is dried and concentrated in vacuo yielding a yellow oil; TLC (silica gel, EtOAc:hexane 1:1) indicates the presence of the desired acid. Further purification by chromatography on silica gel using ethyl acetate:hexane (1:1) as the eluent yields the desired 1-(5-carboxypentyl)-2-(3-pyridyl)-3-methylindole of Example 3.

Workup

  1. filtrationethyl acetate (25 ml, 4:1) and filtered
  2. washThe solid is washed with hot chloroform
  3. concentrationthe combined filtrates concentrated in vacuo
  4. customto yield a dark brown gum which
  5. extractionextracted with 0.1 N aqueous sodium hydroxide (2 ml)
  6. extractionThe aqueous extract
  7. extractionextracted with chloroform
  8. extractionThe chloroform extract
  9. customis dried
  10. concentrationconcentrated in vacuo
  11. customyielding a yellow oil
  12. customFurther purification by chromatography on silica gel

Sources & evidence

ORD record
ord-1103389c7537472cb08f2ff395bbdfb8
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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