A Practical Method for p-Methoxybenzylation of Hydroxy Groups Using 2,4,6-Tris(p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)

Kohei Yamada; Hikaru Fujita; Masanori Kitamura; Munetaka Kunishima

doi:10.1055/s-0033-1339713

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(21): 2989-2997
DOI: 10.1055/s-0033-1339713

paper

A Practical Method for p-Methoxybenzylation of Hydroxy Groups Using 2,4,6-Tris(p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)

Kohei Yamada

Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Fax: +81(76)2646201 eMail: kunisima@p.kanazawa-u.ac.jp

,

Hikaru Fujita

Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Fax: +81(76)2646201 eMail: kunisima@p.kanazawa-u.ac.jp

,

Masanori Kitamura

Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Fax: +81(76)2646201 eMail: kunisima@p.kanazawa-u.ac.jp

,

Munetaka Kunishima*

Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Fax: +81(76)2646201 eMail: kunisima@p.kanazawa-u.ac.jp

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Abstract

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Abstract

A new acid-catalyzed p-methoxybenzylating reagent, 2,4,6-tris(p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM), has been developed. The reaction of acid- and alkali-labile alcohols with TriBOT-PM in the presence of a catalytic amount of various acids (TfOH, BF₃·OEt₂, CSA, etc.) afforded the corresponding p-methoxybenzyl ethers in good yields. Since TriBOT-PM is an air-stable crystalline solid and can be prepared from inexpensive materials, i.e. cyanuric chloride and anisyl alcohol, this route is of practical use.

Key words

benzylation - protecting groups - cations - ethers - alkylation

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Referenzen

References

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