Efficient Flow Synthesis of Glycidyl Ether Using BuSnCl3 as a Mild Lewis Acid

Takayoshi Kasakado; Masahito Nakamura; Akihiro Nishizawa; Tetsuya Hosomi; Ilhyong Ryu; Takahide Fukuyama

doi:10.1055/a-2359-8893

Synthesis, Table of Contents

Synthesis 2024; 56(20): 3142-3146
DOI: 10.1055/a-2359-8893

paper

Flow Chemistry

Efficient Flow Synthesis of Glycidyl Ether Using BuSnCl₃ as a Mild Lewis Acid

Authors

Takayoshi Kasakado

^aOrganization for Research Promotion, Osaka Metropolitan University, Sakai, Osaka 599-8531, Japan
Masahito Nakamura

^bDepartment of Chemistry, Graduate School of Science, Osaka Metropolitan University, Osaka, 558-8585, Japan
Akihiro Nishizawa

^cNagase ChemteX Corporation, Tatsuno, Hyogo 679-4124, Japan
Tetsuya Hosomi

^cNagase ChemteX Corporation, Tatsuno, Hyogo 679-4124, Japan
Ilhyong Ryu

^aOrganization for Research Promotion, Osaka Metropolitan University, Sakai, Osaka 599-8531, Japan

^dDepartment of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu 30010, Taiwan
Takahide Fukuyama ∗

^bDepartment of Chemistry, Graduate School of Science, Osaka Metropolitan University, Osaka, 558-8585, Japan

Abstract

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Abstract

A ring-opening protocol of epichlorohydrin with 2-ethylhexanol was investigated for the synthesis of the corresponding chlorohydrin ether. BuSnCl₃ proved to be an efficient mild Lewis acid catalyst, yielding the product with high selectivity. A scalable flow synthesis was achieved by modifying the flow setup. The flow synthesis of the corresponding glycidyl ether from the chlorohydrin ether was also carried out in an efficient manner by using the basic treatment.

Key words

flow synthesis - glycidyl ethers - epichlorohydrin - BuSnCl₃ - Lewis acids - chlorohydrin

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