07-13-00 18:13
No 28371
.
(Hive Bee)
07-14-00 02:15
No 28501
.
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!
(Stranger)
07-14-00 20:02
No 28776
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. :P(Hive Bee)
07-18-00 01:04
No 29799
what about 2,5 dimethoxy 4-TFM PEA ?
(Hive Bee)
07-18-00 01:18
No 29808
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--
(Hive Bee)
07-18-00 01:23
No 29812
Well there is no point in living if you don't have dreams.
"trip not equal to tryptamine, tryptamine equals trip"
(Moderator)
07-18-00 12:31
No 29984
(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, -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
(Hive Bee)
07-18-00 17:53
No 30056
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
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
(Chief Bee)
07-20-00 22:33
No 31014
Hey Osmium, couldn't you answer this?
http://rhodium.lycaeum.org
(Moderator)
07-21-00 12:34
No 31269
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!