Tetrabutylammonium Fluoride → (e)-1-Fluoro-4-tosyloxy-2-butene
反応式
[S:1]([O:11][CH2:12]/[CH:13]=[CH:14]/[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-:44]>C1COCC1>[F:44][CH2:15]/[CH:14]=[CH:13]/[CH2:12][O:11][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]参加物
4
実験手順
To a solution of (E)-1,4-ditosyloxy-2-butene (256 mg, 0.64 mmol) in 10 mL of THF was added Bu4NF (0.7 mL, 1M in THF, 0.7 mmol). The mixture was heated to reflux for 30 min. Evaporation and purification of the residue by flash column chromatography with hexane:ether/2:1 afforded the product as a colorless oil (60 mg, 38%). 1 H NMR (CDCl3, 300 MHz) δ 7.80 (d, J=8.4 Hz, 2H), 7.36 (d, J=8.4 Hz, 2H), 5.99-5.75 (m, 2H, 4.84 (ddd, JFCH=46.5 Hz, J=4.8, 1.2 Hz, 2H), 4.59-4.56 (m, 2H), 2.46 (s, 3H).