4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent. Issue 21 (16th October 2019)

• Record Type: Journal Article
• Authors: Kobayashi, Shoji; Tamura, Tomoki; Yoshimoto, Saki; Kawakami, Takashi; Masuyama, Araki
• Is Part Of: Chemistry, an Asian journal. Volume 14:Issue 21(2019)
• Page Start: 3921
• Page End: 3937
• Publication Date: 2019-10-16
• Subjects: 2-methyltetrahydrofuran -- 4-methyltetrahydropyran -- green solvent -- organic reaction -- radical; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201901169
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 4‐Methyltetrahydropyran (4‐MeTHP) is a hydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, a comprehensive study on the performance of 4‐MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen‐metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests 4‐MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4‐MeTHP was found incompatible with strong Lewis acids, and the C−O bond was readily cleaved by treatment with BBr3 . Moreover, the radical‐based degradation pathways of 4‐MeTHP, THP and 2‐MeTHF were elucidated on the basis of GC‐MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chemistry perspectives. Abstract : Organic pastures greener : A comprehensive study on the performance of 4‐methyltetrahydropyran (4‐MeTHP) as a reaction solvent is described. The broad applications and higher stability under free‐radical conditions make this solvent a promising alternative to common organic solvents. This study provides key data for process chemists in choosing a reaction solvent under green chemistry perspectives.