Simple and rapid p-methoxybenzylation of hydroxy and amide groups at room temperature by NaOt-Bu and DMSO

[Display omitted] •p-Methoxybenzylation of hydroxy and amide groups using NaOt-Bu in DMSO is described.•Simple, rapid, and cost-effective method.•p-Methoxybenzylation of sterically hindered substrates proceeded at room temperature. The p-methoxybenzylation of hydroxy and amide groups by p-methoxyben...

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Bibliographic Details
Published inTetrahedron letters Vol. 60; no. 48; pp. 151277 - 151280
Main Authors Hamada, Shohei, Sugimoto, Koichi, Iida, Masashi, Furuta, Takumi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.11.2019
Elsevier
Subjects
Chemistry
Chemistry, Organic
DMSO
p-Methoxybenzylation
Physical Sciences
Protecting group
Science & Technology
Sodium tert-butoxide
Protecting group
p-Methoxybenzylation
Sodium tert-butoxide
DMSO
MPM 4-METHOXYBENZYL
SODIUM HYDRIDE
PROTECTION
DEPROTECTION
CATALYST
EFFICIENT METHOD
ALCOHOLS
BENZYL
PMB-ETHERS
CHLORIDE
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Summary:[Display omitted] •p-Methoxybenzylation of hydroxy and amide groups using NaOt-Bu in DMSO is described.•Simple, rapid, and cost-effective method.•p-Methoxybenzylation of sterically hindered substrates proceeded at room temperature. The p-methoxybenzylation of hydroxy and amide groups by p-methoxybenzyl chloride utilizing NaOt-Bu in DMSO is described. p-Methoxybenzylation of sterically hindered menthol using NaOt-Bu in DMSO proceeded faster than the commonly used methods which use NaH in THF or DMF for p-methoxybenzylation of hydroxy and amide groups. The described method was applicable for sterically hindered substrates at room temperature without adding any activating reagents such as tetrabutylammonium iodide.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151277