p-Toluenesulfonic acid → 4-(2-Furyl)-2-butanone
Reaktionsgleichung
[CH3:1][C:2]([CH:4]=[CH2:5])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1>>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:5][CH2:4][C:2](=[O:3])[CH3:1]Komponenten
4
Versuchsvorschrift
Methylvinylketone (14 g, 0.2 mol) was added dropwise over a period of about 2 hours to furan (150 ml), containing a trace of p-toluene-sulphonic acid, boiling under reflux. The dark brown reaction mixture was stirred for about 16 hours at room temperature. The excess furan was removed by distillation, after which the residue was distilled under vacuum giving 4-(2-furyl)butan-2-one (18.5 g, 67% yield). In a way analogous to that described in Example II, the ketone was reduced to the corresponding alcohol and subsequently converted to the mesylate (28 g, 92% yield).