A convenient method for the preparation of 3-trimethylsilyl-2,5-dihydrofurans and their conversion to furans

✍ Scribed by Fumie Sato; Hiroshi Kanbara; Youichi Tanaka

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 193 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)91120-7

✦ Synopsis

Hydromagnesiation of 3-trimethylsilyl-2-propyn-l-01 (&) followed by reaction with aldehydes or ketones affords (E)-3-trimethylsilyl-2-alken-1,4-diols (&), which can be readily dehydrated to 3-trimethylsilyl-2,5-dihydrofurans (3) by treatment with BF30Et2. The compounds 3_ are converted to furans (5) by epoxidation and subsequent treatment with H2S04.

We report here a facile method for the preparation of 3-trimethylsilyl-2,5dihydrofurans (3) from 3-trimethylsilyl-2-propyn-l-01 (l.) via hydromagnesiation,