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

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

Katsuya Saito
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan
,
Tomoya Sawazaki
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan
,
Osamu Furusawa
b   Fukuzyu Pharmacuetical Co., Ltd., 48 Hagiwara, Toyama 939-8261, Japan
,
Teruo Kosugi
b   Fukuzyu Pharmacuetical Co., Ltd., 48 Hagiwara, Toyama 939-8261, Japan
,
Yoshikazu Kimura 
c   Research and Development Department, Iharanikkei Chemical Industry Co. Ltd., Kambara, Shimizu-ku, Shizuoka 421-3203, Japan
,
Masayuki Kirihara 
a   Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan
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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


Publication History

Received: 25 March 2023

Accepted after revision: 05 May 2023

Accepted Manuscript online:
05 May 2023

Article published online:
05 June 2023

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