3,5-dimethoxy-4-trifluoromethylphenethylamine

[Shambhala]

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[zooligan]

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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!

[Shambhala]

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   .  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.  

[Alphabeta121]

what about 2,5 dimethoxy 4-TFM PEA  ?

[psyloxy]

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...

--psyloxy--

[foxy2]

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


"trip not equal to tryptamine, tryptamine equals trip"

[Osmium]

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, -50°C, 6hrs, chlorotrimethylsilane
Silicon containing psychedelics! We are the borgs and you will all be assimilated  
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, -30°C, 2h, I2
 Same works with bromine @ -78°C

[foxy2]

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

"trip not equal to tryptamine, tryptamine equals trip"

[Rhodium]

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

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...

http://rhodium.lycaeum.org

[Rhodium]

Hey Osmium, couldn't you answer this?

http://rhodium.lycaeum.org

[Osmium]

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

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

1-Br-2,4,5-trimethoxybenzene:
J. Org. Chem. 49; 24; 1984; 4657-63 / n-BuLi/tert. amine/Et2O/0°C/1min

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