16576-25-3 → HCID 54321678, 화합물

HRID 2393168노트

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HRID 2393168 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 54321678HCID 54321678, 화합물수율 15.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ebe3346bd6bc4184b5f1d0fd7a70c8ff
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05804601

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