Shambhala (Stranger)
07-13-00 18:13
No 28371
      3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   


(Hive Bee)
07-14-00 02:15
No 28501
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   


Truly enlightening.  It's all clear now.  Thanks!  I think this should definitely go in LaBTop's thread of detailed methods on the newbee board!

07-14-00 20:02
No 28776
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Thank you,  you may now bow and kiss my ring.  I was going to explain to everyone how to make this stuff from table salt & playdough.  Then, I lost track of what I was doing tongue.  You bastard you, heh.  I was simply making an attempt to bring what I though an conversation(thread) from the couch to a place where it might be better off.   :P

(Hive Bee)
07-18-00 01:04
No 29799
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

what about 2,5 dimethoxy 4-TFM PEA  ?

(Hive Bee)
07-18-00 01:18
No 29808
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Why are you always after the ultimate substance, with the ultimate potency ?
Yeah, it's cool but isn't it unreachable for most if not any of us ?

well, that's what I had to say on this...


(Hive Bee)
07-18-00 01:23
No 29812
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Well there is no point in living if you don't have dreams.

"trip not equal to tryptamine, tryptamine equals trip"
07-18-00 12:31
No 29984
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
(Rated as: excellent)

Shame on you bees! Let's get busy and find the necessary refs to save this thread from becoming a farce!

Ok, this being said here is my contribution:

1,2,3-trimethoxybenzene ------> 1,3-dimethoxybenzene

Look at what Ugo Azzena et. al. have to say about it:

Synthesis 1; 1989; 28-30; / K, THF, RT, 24 hrs, 86%!

Tetrahedron Lett. 30; 13; 1989; 1689-90; / K, THF, RT, 24hrs

J. Org. Chem. 55; 19; 1990; 5386-5390; / K, THF, RT, 24hrs

Some other refs useful for this reaction:

J. Chem. Soc. Chem. Commun.; 1987; 1549-50 / K, THF, 87%, olivetol dimethyl ether also included, the one that started it all
J. Org. Chem. 57; 11; 1992; 3101-3106 Good one read it!

Chem. Ber. 44; 1911; 2135; / Na, EtOH; 1,2,3-trimethoxybenzene reduction

Synthesis 1990; 313-14;
1.) trimethoxybenzaldehyde dimethylacetal ---> 4-butyl-3,5-diMeO-benzaldehyde; Na, THF, RT, 53hrs, 86%!!!!
2.) trimethoxybenzaldehyde dimethylacetal ---> 4-ethyl-3,5-diMeO-benzaldehyde; Na, THF, 53hrs, RT, 75%
3.) trimethoxybenzaldehyde dimethylacetal ---> 3,5-dimethoxybenzaldehyde; Na, THF, 53hrs, RT, 92%

Recl. Trav. Chim. Pay-Bas, 109, 7/8; 1990, 443-445; / trimethoxybenzene ---> 1,3-dimethoxy-2-butylbenzene; BuLi, hexane

J. Org. Chem. 55; 19; 1990; 5386-5390; / trimethoxybenzene ---> (2,6-dimethoxyphenyl)trimethylsilane; 1) K, THF, RT, 24hrs; 2) THF, -50C, 6hrs, chlorotrimethylsilane
Silicon containing psychedelics! We are the borgs and you will all be assimilated wink
Lots of useful shit in here (other metals, other electrophiles, substrates, regioselectivity, temp. dependence, product distributions). Get it and read it!

Chem. Ber. 41; 1908; 2556; / Na; EtOH; 5-allyl-1,2,3-trimethoxybenzene ---> 1,3-dimethoxy-5-propylbenzene

J. Chem. Soc. Perkin Trans 1; 3; 1995; 261-266
Tertrahedron Lett. 34; 35; 1993; 5635-38

And the special gift, ready for your favorite trifluoromethylation:

1,2,3-trimethoxybenzene -----> 2-iodo-1,3-dimethoxybenzene:
you guessed right, it another one of those Ugo Azzena refs listed above, the JOC 55 one.

1)K, THF, RT, 24hrs,
2) THF, -30C, 2h, I2
 Same works with bromine @ -78C
(Hive Bee)
07-18-00 17:53
No 30056
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Good work, we should start a trust fund for the moderators.  They deserve it!!!!

"trip not equal to tryptamine, tryptamine equals trip"
(Chief Bee)
07-18-00 18:38
No 30069
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Foxy2: Yes we do. We should have an offshore bank account where our disciples could deposit any donations of excess assets smile

Osmium: Is there any way one could fit a Me3Si- group in the 4-position of 2C-H? Is the Ar-SiMe3 group stable? The procedure above could only be used to make 3,5-MeO-4-TMS-PEA...
(Chief Bee)
07-20-00 22:33
No 31014
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Hey Osmium, couldn't you answer this?
07-21-00 12:34
No 31269
      Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine  Bookmark   

Ok ok boss! But I want some of those new BORGAMINE/SILICAMINE designer drugs! laugh):

1,4-diMeO-benzene ---> 2,5-diMeO-phenyl-TMS: n-BuLi/TMEDA/Et2O/1hr/25C/90%,(Tet. Lett. 36; 45; 1995; 8175-78)
TMEDA/BuLi/Et2O/hexane/RT/24hrs (Tetrahedron 47; 44; 1991; 9279-88 and JOC 49; 24; 1984; 4657-63)

J. Org. Chem. 49; 24; 1984; 4657-63 / n-BuLi/tert. amine/Et2O/0C/1min

Interestingly enough, the TMS group can be removed from aromatics (good way to render a substance temporarily legal! tongue