How to reduce C=C to C-C

[tropine]

Thiking of using Li in ammonia to reduce the double bond in 2,5-dimethoxy-2,5 dihydrofuran, any comments?  I want to avoid Raney Nickel as it is pyrrophoric!

[Rhodium]

And Lithium isn't?

[roger2003]

If you read this JACS -Article, I think, you know more

Post 458701

(Rhodium: "2,5-Dimethoxy-tetrahydrofuran from Furan", Methods Discourse)

[tropine]

thanks for the link, but the JACS article just talks about Raney Nickel again.  Yes Lithium is pyrrophoric, but I thought that Li in liquid ammonia is much less dangerous than Raney Nickel in H2, do you have any experience with Raney Nickel?

[Rhodium]

I thought that Li in liquid ammonia is much less dangerous than Raney Nickel in H₂

I would say the other way around, as long as you have equipment which can take the necessary pressure.

[tropine]

those pressures are just too high for my comfort zone.  The Li in ammonia is well documented on your site rhod, for the reduction of ephedrine.  Mr. Clean's writeup it pretty good, and all precautions are noted.  Chemically however do you think that the reduction will work on the dimethoxydihydrofuran C=C double bond? I am quite sure it will...no pressure and flammable gas, looks like a safer approach to me!

[roger2003]

If you carry out the reduction (or the workup) in aqueous solutions the dimethoxy converts to dihydroxy.

I read this a lot of years ago and cannot find again now.

Ca you send me the JACS article ?