meme (Hive Bee)
03-12-02 16:52
No 281304
      Tryptophol?  Bookmark   

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 wink

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.
(Chief Bee)
03-12-02 19:13
No 281344
      Re: Tryptophol?  Bookmark   

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. 
(Hive Bee)
03-12-02 20:36
No 281374
      Re: Tryptophol?  Bookmark   

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.wink

No barbed wire can cage a bee.
(Master Searcher)
03-13-02 00:33
No 281516
      Re: Tryptophol?  Bookmark   

Look at example 1 here. Patent US3197479
(Hive Bee)
03-29-02 18:18
No 289527
      Substitiued tryptophol?  Bookmark   

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

No barbed wire can cage a bee.
(Chief Bee)
03-29-02 19:09
No 289540
      interference  Bookmark   

Exactly - no interference.
(Hive Bee)
04-01-02 19:18
No 290961
      Asymmetric secondary amines  Bookmark   

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.
04-02-02 00:18
No 291107
      indole with etheleneoxide  Bookmark   

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

Any Possession is a Demonic Possession!
(Chief Bee)
04-02-02 00:33
No 291113
      really?  Bookmark   

Could you back that up with a reference? I thought it only was accessible from indole-3-grignard and ethyleneoxide.
(Distinctive Doe)
04-02-02 07:23
No 291289
      this way too  Bookmark   

I think you could oxidise indole ethylbromide to Tryptophol

Might bee a bit counter productive though

Those who give up essential liberties for temporary safety deserve neither liberty nor safety
04-03-02 03:58
No 291657
      ethylene oxide ref.  Bookmark   

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!
(Hive Bee)
04-04-02 20:45
No 292406
      Thanks  Bookmark   

Thank you Rhodium.

Thank you Foxy.

Thank you Lilienthal.

i found what I was looking for.

No barbed wire can cage a bee.