[AlphaScent]

So friends,

My company has asked me look into making starting materials.  I have been asked to look into making a propargylic alcohol called 1-Hexyn-3-ol.  I want to make it from lithium acetylide and butyraldehyde in liquid ammonia. 

I have looked into using ethynylmagneisum bromide but it is only 1 M solution and is a pain to work with.  It is also not easy to make in the lab. 

My question is, Do you think once the mettalated aceylide is made in situ that the addition of the aldehyde will go off without a hitch? 

Is butyraldehyde going to stand up to liquid ammonia?

[orgopete]

Because you have posted some of your background in another post, let me answer this differently. After one of my early personal reviews, I wrote on my hood, "Stick to what you know works". This has proven to be valuable advice that I have followed many times over. With that frame of mind, thus is what I would do. I'd first look at how it has been prepared in the past, but I wouldn't stop there. Because I am ignorant, I don't know the number of potential routes that may have been tried. If it is a high valuable chemical, it may have been subjected to numerous process patents. Read them. I also find it valuable to read reviews. What chemistry works well and what doesn't.

Because your target is an item of commerce, are you sure you want to make it? If you add your time, chemicals, and variation in yield, would you be better served to buy another company's experience? That simply suggests your task is prepare the target more economically. In that case you need to start adding up the pieces for your proposed route (and I'd include all other routes), the yields you'd need, etc, to begin to estimate possible routes.

By the way, ammonia is going to react with the aldehyde, but I think that is probably only a minor problem. You can change solvents.