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The 1,4 C→O silyl migrations of various furan and thiophene systems

✍ Scribed by Patrick G. Spinazzé; Brian A. Keay

Book ID: 104229726
Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 257 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99574-1

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✦ Synopsis

2-Trialkylsilyl-3-hydroxymethyl-furans and -thiophenes undergo a 1,4 C-O silyl migration when treated with bases containing either potassium or sodium counterions to produce 3-[(trialkylsilyl)oxymethyl]furans and -thiophenes in excellent yields.

We have shown that 3-[(t-butyldimethylsilyl)oxymethyl]furan 3, when treated with n-butyllithiurn/HMPA, undergoes rare a 1,4 0-C sibyl migration producing 2-t-butyldimethylsilyl-3-hydroxymethylfuran 5 (Scheme 1)'

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