Abstract
[1H] Pyrrole (IIa) was reacted with 2-chloroethyl tosylate (III) in acetone in the presence of potassium hydroxide (condition A) to give 1-(4-oxo-2-methyl-2-pentyl) [1H]-pyrrole (IV) instead of 1-(2-tosyloxyethyl) [1H] pyrrole (IIb). IV was obtained from the reaction of IIa and mesityl oxide (V) in acetonitrile in the presence of potassium hydroxide (condition B). With IIa under condition B, crotononitrile, ethyl crotonate, and 4, 4-dimethyl-2-cyclohexenone (IX) gave 3-(1-[1H] pyrrolyl) butyronitrile (VIIa), 3-(1-[1H] pyrrolyl) butyric acid (VIIIa), and a mixture of 4, 4-dimethyl-3-(1-[1H] pyrrolyl) cyclohexanone (X) and 1-cyanomethyl-4, 4-dimethyl-3-(1-[1H] pyrrolyl) cyclohexanol (XI), respectively.
