Vinylmagnesium bromide

Chemical Properties

Clear light brown to brown solution

Uses

Vinylmagnesium bromide solution (1 M in THF) may be used in the synthesis of 2-vinylchroman-4-ones by the conjugate addition with chromones in the presence of a Lewis acid.
It may also be used in the following transformations:

• (S)-3-(benzyloxy)-4-oxo-butanoic acid methyl ester to methyl (3S,4S)-4-hydroxy-3-(phenylmethoxy)hex-5-enoate.
• (R)-1-Azido-5,6-epoxyhexane to (S)-1-(4-azidobutyl)-2-propen-1-ol.
• 2,3-O-Isopropylidene-D-ribose to 1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol.
• (4S,5S)-2,2-Dimethyl-5-vinyl[1,3]dioxolane-4-carbaldehyde to (1R,4R,5S)- and (1S,4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol.
• Ethyl levulinate to ?-methyl-?-vinylbutyrolactone.