Using Red-Al instead of LAH..

[yellium]

As subject says: can you also use red-al to reduce interesting glyoxylamides instead of LAH? The doctor uses it for MBT and 2-Me-DMT, but I'm a bit unsure on the reaction times/temperature for DMT and DET. Anyone got references/info?

(another stupid question: I can't figure out if you need to combine the water wash and the acidic extraction after you've quenched the reaction.)

[terbium]

Is Red-Al any easier to obtain the LiAlH4?

[yellium]

Nope.

And to answer my own question:Red-Al can be used for DMT & friends. After addition at 0'C, a few hours at +40'C  do the job. After quenching & filtering the toluene solution, wash with water to remove the 2-methoxyethanol (yuk!), throw away the water washes, then extract with 0.5M HCl, & do a standard A/B on the HCl extracts. 

[halfapint]

Yellium,

Having answered your own question to your own satisfaction, could you expand on it a bit more in case anyone else might bee interested? I mean, are these glyoxylamides the result of reacting oxalyl chloride with indole and a dialkylamine? I'd suppose so, but you're being stingy with words, for those of us who don't fall asleep with TIhKaL on the pillow. Pray tell, what is Red-Al? Is it the same as the aluminum amalgam as used in the phenylacetone reductive aminations next door? Or is an activated type of aluminum dust? Give me a few more words, make me happy. I've been looking (you wouldn't believe how long) for a reliable, verified alternative to LAH in that particular reduction, and to be tittilated by a cryptic teaser like this is frustrating. So please say it again, but just tell me what you're talking about this time.

turning science fact into << science fiction >>

[terbium]

Red-Al (AKA Vitride) is a toluene solution of sodium bis(2-methoxyethoxy)aluminum hydride. It is available from a major U.S. based supplier of organic reagents.

Its only advantage over LiAlH4 is that it is a liquid which makes it easy to work with in large quantities than LAH.

[yellium]

Another advantage is that it reacts quicker than LiAlH4. LAH reductions usually take a day at reflux; Red-Al reductions can be done in a few hours. But it is indeed a more esoteric chemical.

halfapint: yup, these amides were obtained using the oxalylchloride/indole/dialkylamine route. Red-Al isn't OTC. OTOH, if you're in a position where you could order oxalylchloride, I think the Red-Al wouldn't be much of a problem.

[Rhodium]

A disadvantage is that it is more expensive than LAH per available hydride ion.

http://rhodium.lycaeum.org

[yellium]

Yup, about 5 times.