Methyl vinyl ketone → HCID 19065568, Verbindung

Reaktionsgleichung

[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=[O:11])=[CH:4][CH:3]=1.[CH:17]([C:19]([CH3:21])=[O:20])=[CH2:18].C(N(CC)CC)C>C(O)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:10](=[O:11])[CH2:18][CH2:17][C:19](=[O:20])[CH3:21])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Komponenten

Versuchsvorschrift

To a stirred solution of 3-(4-fluorophenoxy)benzaldehyde (26.8 g; 0.124M) in ethanol (60 ml) was added methyl vinyl ketone (8.32 ml; 0.1M), 3-benzyl-5-(2-hydroxyethyl)-4-methylthizolium chloride (5.93 g; 0.022M), and triethylamine (27.88 ml; 0.2M) at room temperature. After stirring for 6 hrs, volatiles were removed. To the residue was added water (200 ml), and the whole was extracted with ethyl acetate (150 ml×2). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over MgSO4, and concentrated in vacuo. The residual oil was purified by flash column (SiO2) eluting with ethyl acetate-n-hexane (1:5) to give 19.03 g (yield 66.5%) of the subtitle compound [C] as a pale yellow oil.