Synthetic Communications p. 1051 - 1056 (2006)
Update date:2022-08-03
Topics: Synthesis Characterization Catalyst Isolation reflux Nucleophilic substitution Acetic acid Spectroscopy Reaction Vessel Diethyl ether 7-formyl-indole 7-hydroxy-indole
Uchil, Vinod R.
Gund, Machhindra
Satyam, Apparao
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 pivaloyl or tetrahydropyranyl group, the yields of 4 are increased to 39% and 48%, respectively. Finally, 4 is oxidized with pyridinium chlorochromate (PCC) to afford 5 in 86% yield. Copyright Taylor & Francis Group, LLC.
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