16576-25-3 → HCID 54321678, compound

HRID 2393168Notes

Reaction equation

HRID 2393168 reaction equation
[C:1]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:22])=[O:21].CC(C)([O-])C.[K+]>CS(C)=O.O>[C:2]1([C:1]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:27][CH2:26][CH2:25][CH2:24][CH2:23][C:20]([OH:22])=[O:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 72702916576-25-3HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 54321678HCID 54321678, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-benzoylquinoline (4.0 g) and (5-carboxy-l-pentyl)triphenylphosphonium bromide (11.8 g) in DMSO (50 ml) was added potassium t-butoxide (5.8 g) gradually and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was poured in iced water and washed with toluene. The aqueous layer was neutralized with 3N HCl and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried and the solvent was distilled off. The crude residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1) to give 0.90 g of 7-phenyl-7-(2-quinolyl)-6-heptenoic acid as a mixture of its (E) and (Z) forms. This mixture (0.90 g) and 5% palladium-on-carbon (0.90 g) were suspended in methanol (10 ml) and stirred in a hydrogen atmosphere at room temperature for 3 hours. The catalyst was then filtered off and the filtrate was concentrated to provide the title compound (1.0 g).

Workup

  1. washwashed with toluene
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe crude residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ebe3346bd6bc4184b5f1d0fd7a70c8ff
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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