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
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: