Formaldehyde → 4-Benzyloxy-1-hydroxymethylindole

Participants

Reaction Steps

Compounds of Formula I also can be prepared as illustrated by exemplary reaction in Scheme 2. Reaction of 4-benzyloxy-indole with formaldehyde in the presence of a base such as NaOH produced 4-benzyloxy-1-hydroxymethyl-indole. The benzyl protecting group was removed by hydrogenation to give the 4-hydroxy-1-hydroxymethyl-indole. Reaction of 4-hydroxy-1-hydroxymethyl-indole with an aryl-aldehyde, such as 5-bromoveratraldehyde and malononitrile in the presence of a base, such as piperidine produced the substituted 7-hydroxymethyl-pyrrolo[2,3-h]chromene.

Provenance & Evidence