Reaktion #4617

Reaktionsgleichung

3-(3,4-methylenedioxybenzoyl)pyridine

Sodium hydride

dimethyl sulfoxide

5-carboxypentyltriphenylphosphonium bromide

→

(Z)-7-(3,4-methylenedioxyphenyl)-7-(3-pyridyl)-6-heptenoic acid

Ausbeute 24.6%

Lösungsmittel

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   workup.STIRRINGThe mixture was stirred for 10 minutes
3. 3
   workup.ADDITIONAfter completion of addition
4. 4
   workup.STIRRINGthe mixture was further stirred at room temperature for 30 minutes
5. 5
   workup.ADDITIONwas added
6. 6
   Extraktionthe neutral substance was extracted twice with toluene (50 ml)
7. 7
   Extraktionextracted with ethyl acetate
8. 8
   WaschenThe organic layer was washed with water
9. 9
   Trocknendried (magnesium sulfate)
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    EinengenThe eluate was concentrated
12. 12
    Sonstigethe residue was crystallized from ethyl acetate-isopropyl ether

Vorschrift

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.

Quelle