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Selective deprotection of silyl-protected phenols using solid NaOH and a phase transfer catalyst

✍ Scribed by R.David Crouch; Mike Stieff; Jessica L. Frie; Amy B. Cadwallader; Daniel C. Bevis

Book ID
104261245
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
212 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aryl silyl ethers can be deprotected to yield phenols in good to excellent yields using a biphasic system of 10 equivalents of NaOH and catalytic Bu4NHSO4 in 1,4dioxane. Alkyl silyl ethers prepared using a variety of silyl protecting groups survive under these conditions, allowing selective deprotection of silyl-protected phenols in the presence of silyl-protected alcohols.

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