New Application of Bromotrimethylsilane: Elaboration of Aldehydes/Ketones into Homologous α,β‐Unsaturated Esters via β‐Hydroxy Esters

Abstract

α,β‐Unsaturated esters are formed when β‐hydroxy esters react with bromotrimethylsilane which is generated from chlorotrimethylsilane‐lithium bromide in acetonitrile.

^#Dedicated to Professor Goverdhan Mehta on his 60th birthday.

Keywords:

• Bromotrimethylsilane
• β‐hydroxy ester
• reformatsky reaction
• α,β‐unsaturated ester
• β,γ‐unsaturated ester

Acknowledgment

The financial grant from Space and Missile Division, Air Force Research Laboratory, Edwards Air Force Base, CA to support this research is gratefully acknowledged. The author thanks Dr. Ronald Channell, Mr. Michael Huggins, and Mr. Ronald Bates for their encouragement. The help rendered by Ms. Amanda Schoettmer in running low‐resolution GC‐Mass is highly appreciated.

Notes

^#Dedicated to Professor Goverdhan Mehta on his 60th birthday.

¹β‐Hydroxy esters can also be prepared from α‐trimethylsilylester and aldhyde/ketone in the presence of fluoride ion