OK, one more:
                               
Indole + H₂CO ^__> 3-indolemethanol 82%, when refluxed for 6 h in CH₃O Na.

If substituting ethanol yeilded tryptophol, even in a lessened yeild, I'd be a happy bee  

OK, here's the ref, as complete as it was in the book, and the book itself:

Ref. 15 Vol. 1 p 171

Buehler and Pearson.  Survey of Organic Synthesis .  Wiley-Interscience.  New York, 1970.

I have some more coming

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No barbed wire can cage a bee.

No, ethanol does not add to indole, even if you are begging the molecule on your knees... However, you can make the grignard reagent Indole-3-magnesium bromide (as detailed in another post in this forum) and react that with ethylene oxide (oxirane, ethene epoxide) - the result after aqueous hydrolysis is Tryptophol.

Thanks, Rhodium, you're the greatest.  I had a wonderful week last week just reading, amazing really.  Thanks for inspiring me to post refs, you can't imagine what that's doing to me.

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No barbed wire can cage a bee.

Look at example 1 here.

Patent US3197479

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http://www.geocities.com/dritte123/PSPF.html

Can I take it that substitutions (on the 4 and 5) don't adversely affect this?

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No barbed wire can cage a bee.

Exactly - no interference.

OK, would the tryptophol method work as well for asymmetric secondary amines, such as n-methyl, n-isopropylamine, et al.?  What about primary amines?

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No barbed wire can cage a bee.

I do beleive that tryptophol can be obtained from indole and etheleneoxide*BF3,
in a typical electrophilic substitution way.
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Z_Hound

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Any Possession is a Demonic Possession!

Could you back that up with a reference? I thought it only was accessible from indole-3-grignard and ethyleneoxide.

I think you could oxidise indole ethylbromide to Tryptophol


Might bee a bit counter productive though

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Those who give up essential liberties for temporary safety deserve neither liberty nor safety

Examples of electrophilic substituion
 using oxirane with some benzenes are:

J. Soc. chem. Ind. Japan Spl.; 44; 1941; 284.

Journal; Smith; Natelson; JACSAT; J.Amer.Chem.Soc.; 53; 1931; 3476, 3479.
 Journal; Colonge; Rochas; BSCFAS; Bull.Soc.Chim.Fr.; 1948; 825.


with indole i did not find anything like that; using bbeilstein commander, yet,
but it seems quite likely .

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Any Possession is a Demonic Possession!

Thank you Rhodium.

Thank you Foxy.

Thank you Lilienthal.

i found what I was looking for.

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No barbed wire can cage a bee.