Abstract A simple route to 7??formyl??indole (5) is described in which appropriately functionalized o??nitrotoluenes (1) are converted to 7??hydroxymethyl??indole (4) using the Batcho–Leimgruber process. Condensation of 3??methyl??2??nitrobenzyl alcohol (1a) with N, N??dimethylformamide dimethyl acetal yields the enamine 2a, which upon catalytic hydrogenation affords 4 in 22% yield. When the hydroxyl function in 1 is protected with ...
[Reggelin, Michael; Junker, Bernd; Heinrich, Timo; Slavik, Stefan; Buehle, Philipp Journal of the American Chemical Society, 2006 , vol. 128, # 12 p. 4023 - 4034]