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The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: meme on March 12, 2002, 04:52:00 PM

Title: Tryptophol?
Post by: meme on March 12, 2002, 04:52:00 PM
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 :)
No barbed wire can cage a bee.
Title: Re: Tryptophol?
Post by: Rhodium on March 12, 2002, 07:13:00 PM
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.
Title: Re: Tryptophol?
Post by: meme on March 12, 2002, 08:36:00 PM
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. ;)
No barbed wire can cage a bee.
Title: Re: Tryptophol?
Post by: PolytheneSam on March 13, 2002, 12:33:00 AM
Look at example 1 here.

Patent US3197479 (http://l2.espacenet.com/dips/viewer?PN=US3197479&CY=gb&LG=en&DB=EPD)


http://www.geocities.com/dritte123/PSPF.html
Title: Substitiued tryptophol?
Post by: meme on March 29, 2002, 06:18:00 PM
Can I take it that substitutions (on the 4 and 5) don't adversely affect this?
No barbed wire can cage a bee.
Title: interference
Post by: Rhodium on March 29, 2002, 07:09:00 PM
Exactly - no interference.
Title: Asymmetric secondary amines
Post by: meme on April 01, 2002, 07:18:00 PM
OK, would the tryptophol method work as well for asymmetric secondary amines, such as n-methyl, n-isopropylamine, et al.?  What about primary amines?
No barbed wire can cage a bee.
Title: indole with etheleneoxide
Post by: Z_Hound on April 02, 2002, 12:18:00 AM
I do beleive that tryptophol can be obtained from indole and etheleneoxide*BF3,
in a typical electrophilic substitution way.
-----
Z_Hound




Any Possession is a Demonic Possession!
Title: really?
Post by: Rhodium on April 02, 2002, 12:33:00 AM
Could you back that up with a reference? I thought it only was accessible from indole-3-grignard and ethyleneoxide.
Title: this way too
Post by: foxy2 on April 02, 2002, 07:23:00 AM
I think you could oxidise indole ethylbromide to Tryptophol
;D

Might bee a bit counter productive though
:)
Those who give up essential liberties for temporary safety deserve neither liberty nor safety
Title: ethylene oxide ref.
Post by: Z_Hound on April 03, 2002, 03:58:00 AM
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 .



Any Possession is a Demonic Possession!
Title: Thanks
Post by: meme on April 04, 2002, 08:45:00 PM
Thank you Rhodium.

Thank you Foxy.

Thank you Lilienthal.

i found what I was looking for.
No barbed wire can cage a bee.
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