So this what i've been working on lately. Im gonna have 0 time to pursue this in the following months so i defer to you guys for improvements/ results if any of you are interested.
I've been trying to improve twodogs method ( MDA synthesis from alpha-methyl-1,3-benzodioxole-5-propanal via Oxime and then Hoffman ) by using a one pot reaction that leads directly from alpha-methyl-1,3-benzodioxole-5-propanal to the corresponding Amide with fairly OTC chemicals.
Here are the references ( i believe you can even find them online) :
1) J. Org. Chem. 2003, 68, 1158-1160
2) Tetrahedron Letters 42 (2001) 1103–1105 ( Pretty much the same thing )
For those of you who can't access this. Basically the reaction uses a nitrile intermediary. What you do is react alpha-methyl-1,3-benzodioxole-5-propanal with Iodine in 27% Ammonia water for approx one hour ( no heat) then drop H2O2 slowly to the mixture and VOILA. Wash, extract with DCM and ideally you have the Amide.
Thats in theory. Now the fun part.
The only thing that bothered me in this write up was the use of THF as cosolvent with water and the use of 27% ammonia. I've been trying to find another cosolvent and use only 13 % Ammonia ( with the right adjustments to xxxxxxxx proportions) to make this MEGA OTC but what this has been giving me is mostly crapola. The main issue being the I2 wasnt dissolving properly.
There you go. Give me your thoughts / improvements although i wont be able to put them into practice before late this summer..
It'd be great if some of you could run it but i guess thats just wishful thinking ^^
Cheers
I've been trying to improve twodogs method ( MDA synthesis from alpha-methyl-1,3-benzodioxole-5-propanal via Oxime and then Hoffman ) by using a one pot reaction that leads directly from alpha-methyl-1,3-benzodioxole-5-propanal to the corresponding Amide with fairly OTC chemicals.
Here are the references ( i believe you can even find them online) :
1) J. Org. Chem. 2003, 68, 1158-1160
2) Tetrahedron Letters 42 (2001) 1103–1105 ( Pretty much the same thing )
For those of you who can't access this. Basically the reaction uses a nitrile intermediary. What you do is react alpha-methyl-1,3-benzodioxole-5-propanal with Iodine in 27% Ammonia water for approx one hour ( no heat) then drop H2O2 slowly to the mixture and VOILA. Wash, extract with DCM and ideally you have the Amide.
Thats in theory. Now the fun part.
The only thing that bothered me in this write up was the use of THF as cosolvent with water and the use of 27% ammonia. I've been trying to find another cosolvent and use only 13 % Ammonia ( with the right adjustments to xxxxxxxx proportions) to make this MEGA OTC but what this has been giving me is mostly crapola. The main issue being the I2 wasnt dissolving properly.
There you go. Give me your thoughts / improvements although i wont be able to put them into practice before late this summer..
It'd be great if some of you could run it but i guess thats just wishful thinking ^^
Cheers


