Synlett 2004(10): 1802-1804  
DOI: 10.1055/s-2004-829550
LETTER
© Georg Thieme Verlag Stuttgart · New York

Lithium Hexafluorophosphate-Catalyzed Efficient Tetrahydropyranylation of Tertiary Alcohols under Mild Reaction Conditions

Nao Hamada, Tsuneo Sato*
Department of Chemistry and Bioscience, Kurashiki University of Science and the Arts, Kurashiki 712-8505, Japan
Fax: +81(86)4401062; e-Mail: sato@chem.kusa.ac.jp;
Further Information

Publication History

Received 26 March 2004
Publication Date:
15 July 2004 (online)

Abstract

Lithium hexafluorophosphate is found to be an efficient catalyst for the tetrahydropyranylation of tertiary alcohols with dihydropyran under mild reaction conditions.

15

The use of KPF6 instead of LiPF6 did not affect the protection at all.

16

The Lewis acidity of lithium ion decreases when lithium ion is stabilized by coordinative solvation.

17

Although testosterone is slightly soluble in hexane, quantitative tetrahydropyranylation was possible by using longer reaction times.

18

Purchased from Kishida Chemical Co., Ltd.