Dimethyl Sulfoxide → (Z)-7-phenyl-7-pyridin-3-ylhept-6-enoic acid

HRID 845732

반응식

HRID 845732 반응식
CS(C)=O.[H-].[Na+].[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:35]([C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1)(=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.O1CCCC1>[N:45]1[CH:46]=[CH:47][CH:48]=[C:43](/[C:35](/[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:15]\[CH2:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])[CH:44]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 21540Phenyl-3-pyridinylmethanoneHCID 24758Sodium hydrideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromide

생성물 1

HCID 6537201(Z)-7-phenyl-7-pyridin-3-ylhept-6-enoic acid수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To dimethylsulfoxide (40 ml) was added dropwise sodium hydride (1.0 g), and the mixture was heated at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, to which was added 5-carboxypentyltriphenyl phosphonium bromide (9.5 g, 21 mmoles) and the mixture was stirred for 5 minutes. To the reaction mixture was added a tetrahydrofuran solution (10 ml) of 3.7 g (0.02 mole) of 3-benzoylpyridine. The mixture was stirred for 30 minutes at room temperature, followed by addition of water (100 ml), which was subjected to extraction twice with ethylacetate (50 ml). The aqueous layers were combined and adjusted to pH 6 with 2N HCl, which was subjected to extraction with ethyl acetate. The organic layers were combined and washed with water and dried (magnesium sulfate). The solvent was then evaporated off, and the residue was subjected to silica-gel chromatography, using ethanolethyl acetate (1:5) as eluant to yield (E)+(Z)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (Ia-3, Ia-4 in Table 3) (4.5 g 79%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature, to which
  2. stirringThe mixture was stirred for 30 minutes at room temperature
  3. extractionwas subjected to extraction twice with ethylacetate (50 ml)
  4. extractionwas subjected to extraction with ethyl acetate
  5. washwashed with water
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was then evaporated off

출처 및 근거

ORD 기록
ord-02672fc4522e4dbcb4507e74ae085a98
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04760068

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