I have a reference that adds an aliphatic Grignard to propylene oxide utilizing catalytic CuI. They do report minor Wurtz products which is kind of annoying. I am going to try it because it is an easy reaction.
I have a reference that adds an aliphatic Grignard to propylene oxide utilizing catalytic CuI. They do report minor Wurtz products which is kind of annoying. I am going to try it because it is an easy reaction.
Best to make the dialkyl magnesium cuprate and make BF3-complex, then mix with the epoxide. I think its simmilar to dialkyl lithium cuprates. I have reacted grignard with secondary epoxide with good yield so I am not sure if cuprate is neccesary. HMPA would probably speeed things up. In your case the epoxide is not sterically hindered so maybe its very easy.
Best to make the dialkyl magnesium cuprate and make BF3-complex, then mix with the epoxide. I think its simmilar to dialkyl lithium cuprates. I have reacted grignard with secondary epoxide with good yield so I am not sure if cuprate is neccesary. HMPA would probably speeed things up. In your case the epoxide is not sterically hindered so maybe its very easy.
Addition of Grignard reagents to ethylene oxide, is described in various editions of the Vogel’s Textbook of Practical Organic Chemistry (Chapter: Aliphatic alcohols). For example, in the 5th Edition, this corresponds to the pages 535-537. However, the obtained yields are rather moderate (50-70%). Anyway and in the case of propylene oxide, you will get a mixture of alcohols and the secondary alcohol will probably be the major product.
Addition of Grignard reagents to ethylene oxide, is described in various editions of the Vogel’s Textbook of Practical Organic Chemistry (Chapter: Aliphatic alcohols). For example, in the 5th Edition, this corresponds to the pages 535-537. However, the obtained yields are rather moderate (50-70%). Anyway and in the case of propylene oxide, you will get a mixture of alcohols and the secondary alcohol will probably be the major product.
You saw no Payne rearrangement?
I have a reference that adds an aliphatic Grignard to propylene oxide utilizing catalytic CuI. They do report minor Wurtz products which is kind of annoying. I am going to try it because it is an easy reaction.
We shall see.
Cheers!
You saw no Payne rearrangement?
I have a reference that adds an aliphatic Grignard to propylene oxide utilizing catalytic CuI. They do report minor Wurtz products which is kind of annoying. I am going to try it because it is an easy reaction.
We shall see.
Cheers!
More
VOTE
https://pubs.acs.org/doi/10.1021/jo00009a012
https://pubs.acs.org/doi/10.1021/jo00009a012
More
VOTE
More
VOTE
Anyway and in the case of propylene oxide, you will get a mixture of alcohols and the secondary alcohol will probably be the major product.
Anyway and in the case of propylene oxide, you will get a mixture of alcohols and the secondary alcohol will probably be the major product.
More
VOTE