Practical Synthesis of Pent-4-yn-1-ol and Pent-4-en-1-ol from Tetrahydrofurfuryl Halides

Katsuya Saito; Tomoya Sawazaki; Osamu Furusawa; Teruo Kosugi; Yoshikazu Kimura; Masayuki Kirihara

doi:10.1055/a-2088-1624

Synthesis, Table of Contents

Synthesis 2023; 55(17): 2670-2673
DOI: 10.1055/a-2088-1624

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Practical Synthesis of Pent-4-yn-1-ol and Pent-4-en-1-ol from Tetrahydrofurfuryl Halides

Katsuya Saito

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan

,

Tomoya Sawazaki

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan

,

Osamu Furusawa

^bFukuzyu Pharmacuetical Co., Ltd., 48 Hagiwara, Toyama 939-8261, Japan

,

Teruo Kosugi

^bFukuzyu Pharmacuetical Co., Ltd., 48 Hagiwara, Toyama 939-8261, Japan

,

Yoshikazu Kimura

^cResearch and Development Department, Iharanikkei Chemical Industry Co. Ltd., Kambara, Shimizu-ku, Shizuoka 421-3203, Japan

,

Masayuki Kirihara

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan

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Abstract

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Abstract

Pent-4-yn-1-ol was prepared in a high yield by the reaction of tetrahydrofurfuryl chloride with n-BuLi in t-BuOMe at 0 °C. Pent-4-en-1-ol was prepared in a high yield by either the reaction of tetrahydrofurfuryl chloride or tetrahydrofurfuryl bromide with lithium in tetrahydrofuran at temperatures from 0 °C to ambient temperature.

Key words

pent-4-yn-1-ol - tetrahydrofurfuryl chloride - n-butyllithium - t-butyl methyl ether - pent-4-en-1-ol - tetrahydrofurfuryl bromide - lithium - tetrahydrofuran

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References

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