Dimethyl Sulfoxide → 7-Benzo[1,3]dioxol-5-yl-7-pyridin-3-yl-hept-6-enoic acid

HRID 4521

Reaktionsgleichung

Reaktionsgleichung von HRID 4521
[H-].[Na+].CS(C)=O.[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].[CH2:35]1[O:51][C:50]2[CH:49]=[CH:48][C:39]([C:40]([C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=O)=[CH:38][C:37]=2[O:36]1>O1CCCC1.O>[CH2:35]1[O:51][C:50]2[CH:49]=[CH:48][C:39](/[C:40](/[C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[CH:15]/[CH2:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])=[CH:38][C:37]=2[O:36]1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 13285824(2H-1,3-Benzodioxol-5-yl)(pyridin-3-yl)methanone

Produkt 1

HCID 132858317-Benzo[1,3]dioxol-5-yl-7-pyridin-3-yl-hept-6-enoic acidAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Sodium hydride (1 g, 60% in oil) was added to dimethyl sulfoxide (25 ml) under nitrogen and the mixture was heated at 85° C. with stirring for an hour. The reaction mixture was cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (5.2 g, 11 mmoles) was added gradually. The mixture was stirred for 10 minutes and a solution of 3-(3,4-methylenedioxybenzoyl)pyridine (2.5 g, 0.11 mole) in tetrahydrofuran (10 ml) was added dropwise thereto. After completion of addition, the mixture was further stirred at room temperature for 30 minutes. After completion of the reaction, water (100 ml was added and the neutral substance was extracted twice with toluene (50 ml). The aqueous layer was adjusted to pH 5.5 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as the eluent. The eluate was concentrated and the residue was crystallized from ethyl acetate-isopropyl ether to give (Z)-7-(3,4-methylenedioxyphenyl)-7-(3-pyridyl)-6-heptenoic acid (0.4 g, 24.6%). Mp 90°-91° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred for 10 minutes
  3. additionAfter completion of addition
  4. stirringthe mixture was further stirred at room temperature for 30 minutes
  5. additionwas added
  6. extractionthe neutral substance was extracted twice with toluene (50 ml)
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated under reduced pressure
  11. concentrationThe eluate was concentrated
  12. customthe residue was crystallized from ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a74b6d8de3c74927ba4f80b2e8d86f3c
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727078

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