[jgrayczyk]

Hello,
I am working on synthesizing a primary allyamine and am having trouble with my workup procedure. I am using LAH in ether at 35°C however I am losing most of my product during the workup. I have tried numerous other reagents such as Red-Al, DIBAL, LiBH4, and NaBH4. I have tried the Feiser method and Rochelle's salt multiple times with zero yield, acid workup, basic workup, acetic acid, EtOAc, methanol,and just plain water. I am unsure of any other procedures and am at a standstill right now. Any help would be appreciated

[wildfyr]

Care to tell us more about your synthesis procedure? Such hydride salts have terrible solubility in diethyl ether, perhaps using THF would help. It would also allow you to heat it more.

What is the starting material? If you're coming from an azide a Staudinger type reaction will probably work better, though I have seen some truly truly mild azide-->amine reductions out there reagent sets like like Zn(0) and ammonium chloride

http://www.tandfonline.com/doi/abs/10.1081/SCC-120014032

[jgrayczyk]

I have tried THF before and it does not seem to help much at all. I am reducing the primary amide on an aliphatic chain.

[rolnor]

Do you monitor the reaction by TLS or other way?

[jgrayczyk]

I have not yet been able to monitor the reaction in any specific way. I have been using an internal standard for NMR after workup but that has only resulted in yields less than 40% with one being 63% but unreproducible.