Chemical Properties
CLEAR LIGHT YELLOW TO BROWN LIQUID
Uses
1-Methoxy-3-trimethylsilyloxy-1,3-butadiene is used as a highly reactive diene for Diels-Alder reactions and hetero-Diels-Alder reactions.
Preparation
1-Methoxy-3-trimethylsilyloxy-1,3-butadiene was originally prepared from 4-Methoxy-3-buten-2-one with Chlorotrimethylsilane-Triethylamine-Zinc Chloride in benzene as shown below (68% yield, eq 1). At the present time, the most efficient method is to use TMSCl-Lithium Bromide-Et3N in THF (91%).
storage
1-Methoxy-3-trimethylsilyloxy-1,3-butadiene can be kept in a stoppered container without appreciable decomposition, but it is extremely moisture sensitive.
