Water → 2,2-Dimethyl-7-phenyl-7-pyridin-3-yl-hept-6-enoic acid

HRID 463053

Reaktionsgleichung

Reaktionsgleichung von HRID 463053
[Br-].[C:2]([C:5]([CH3:30])([CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[H-].[Na+].[C:33]([C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)(=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>CS(C)=O.C1(C)C=CC=CC=1>[CH3:29][C:5]([CH3:30])([CH2:6][CH2:7][CH2:8]/[CH:9]=[C:33](/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)\[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[C:2]([OH:4])=[O:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 21540Phenyl-3-pyridinylmethanoneHCID 24758Sodium hydrideHCID 861086235-Carboxy-5,5-dimethylpentyltriphenylphosphonium bromide

Produkt 1

HCID 134172912,2-Dimethyl-7-phenyl-7-pyridin-3-yl-hept-6-enoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Carboxy-5,5-dimethylpentyltriphenylphosphonium bromide (3 g, 6 mmole) was dissolved in anhydrous dimethylsulfoxide (30 ml) under a nitrogen atmosphere, and sodium hydride (0.25 g, 64 mmole) was added to the solution at 30° to 35° C., followed by stirring at 25° to 30° C. for 30 minutes. 3-Benzoylpyridine (0.9 g, 5 mmole) was added to the solution, followed by stirring at room temperature for another 1 hour. Water (100 ml) and toluene (100 ml) were added to the reaction solution, the organic layer was separated, and the water layer was adjusted to pH 6.0 with 2N hydrochloric acid. The product was extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel, and development was effected with ethyl acetate to yield (E+Z)-2,2-dimethyl-7-phenyl-7-(3-pyridyl)-6-heptenoic acid (2-a, 2-b) (1.36 g, 88%).

Aufarbeitung

  1. stirringby stirring at room temperature for another 1 hour
  2. customthe organic layer was separated
  3. extractionThe product was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a column of silica gel, and development

Quellen und Nachweise

ORD-Eintrag
ord-e9fb7c31851b4d4fb6ab6f36a8d5ea52
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518602

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