Isopropanol → 3-phenylthiophene-2-carboxylic Acid

反応式

CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]1([C:20]2[CH:24]=[CH:23][S:22][C:21]=2[CH:25]=[O:26])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(C)C>CC(C)=O>[C:14]1([C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:25]([OH:3])=[O:26])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

実験手順

8N Jones' reagent (ca. 10 ml) was added dropwise to a solution of 3-phenylthiophen-2-aldehyde (5) (0.58 g, 3.1 mmol) in 32 ml of acetone, until an orange colour persisted. The mixture was stirred at room temperature for 18 hrs. Isopropanol (5 ml) was added to remove the excess Jones' reagent and the mixture was then filtered, the organic solvents were evaporated under vacuum and extracted with ethyl acetate (4×100 ml). The combined organic layer was washed with a saturated solution of NaCl, dried (Na2SO4), and evaporated under reduced pressure. The mixture was then chromatographed using 95/5 chloroform/methanol, thus giving the compound (6) (0.44 g, 1.36 mmol, 46% yield) (M.Pt. 200-202° C.). 1H-NMR (CDCl3) ä 6.87-7.37 (m, 5H, Ph-H), 7.05 (d J=5.0 Hz, 1H, th-H4), 7.53 (d J=5.0 Hz, 1H, th-H5).