Water → 1-(Quinolin-6-yl)but-1-ene-3-one

HRID 2118854

Reaktionsgleichung

Reaktionsgleichung von HRID 2118854
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21](=[O:23])[CH3:22])C=CC=CC=1.O>CS(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH:20][C:21](=[O:23])[CH3:22])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 7656536-Quinolinecarbaldehyde

Produkt 1

HCID 538456471-(Quinolin-6-yl)but-1-ene-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of quinoline-6-carboxaldehyde (5.29 g) and 1-triphenylphosphoranylidene-2-propanone (1.5 equiv) in dimethyl sulfoxide (100 ml) was stirred at room temperature for 24 hr. The solution was poured into water (600 ml) which was subsequently extracted with ethyl acetate. The dried (MgSO4) organic fraction was evaporated under reduced pressure and the residue was purified by column chromatography over silica with dichloromethane/ethyl acetate (4:1 v/v) elution to give 1-(quinolin-6-yl)but-1-ene-3-one as a white solid. Pmr spectrum (CDCl3 ; δ in ppm): 2.41 (3H,s); 6.83 (1H,d); 7.3-9.0 (7H,m).

Aufarbeitung

  1. extractionwas subsequently extracted with ethyl acetate
  2. dry with materialThe dried (MgSO4) organic fraction
  3. customwas evaporated under reduced pressure
  4. customthe residue was purified by column chromatography over silica with dichloromethane/ethyl acetate (4:1 v/v) elution

Quellen und Nachweise

ORD-Eintrag
ord-5dac0518cfc3437fa953b7348b5e0324
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04680400

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