Indolylacetic to triptophol

[Antoncho]

the idea isn't exactly mine but it was undeservedly forgotten anyway

i remember having seen a reference on the hive that stated that refluxing tryptofol with dimethylamine/Raney Ni in alc. soln gives DMT in good yields. no further details were given, but i think that sentence already contains everything one needs exept the rxn time.
Keeping in mind that along with the following facts:

1) Raney Ni is easily made by thermal decomposition of Ni oxalate/ formate

2) tryptofol is only one reduction away from indolylacetic acid (heteroauxin - sodium indolylacetate)

3) heteroauxin is freely available from plant supply stores

4) all other DMT synths require LAH that is so fuckin inaccessible to many of us

, the following obvious questions arise:

1) what of the following reagents can be used for reducing IAA to tryptofol:
            a) sodium in EtOH
            b) Al isopropoxide
            c) Al amalgam
            d) tin (II) cloride
2) are there any other simple methods for acid to alcohol reduction?


i sincerely hope that i got some of you bees interested

Antoncho

[ragga]

i'm intrested but have nothing to offer yet.

[smiley_boy]

This doesn't quite make sense; where did this idea originate from? What exactly do you mean by 'triptophol'? If its 2-(indole-3-yl)-ethanol, then I seriously doubt it could work that way.

Still, indole acetic acid can readily be used as a starting material for producing DMT. By condensing indole-3-yl-acetic acid with dimethylamine, you have 2-(indole-3-yl)-acetic acid dimethyl amide. If you then reduce the amide, you have DMT. This last reduction can be accomplished using a number of different reducing agents.

But this is certainly not a new idea. This has been used in the literature, and, has been discussed here before.