16576-25-3 → HCID 54321678、化合物

HRID 2393168ノート

反応式

HRID 2393168 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 54321678HCID 54321678、化合物収率 15.8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ebe3346bd6bc4184b5f1d0fd7a70c8ff
出典データセット
uspto-grants-1998_09
特許番号
US05804601

反応ノート

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