2-(Methylthio)tetrahydrofuran

[98194-87-7]  · C5H10OS  · 2-(Methylthio)tetrahydrofuran  · (MW 118.22)

(methanethiol carbanion, HSCH2-, equivalent1)

Physical Data: bp 66-67 °C/21 mmHg; n20D 1.4868.2

Preparative Methods: conveniently prepared in two steps in 46% yield from THF by light-initiated a-chlorination with Sulfuryl Chloride at -30 °C followed by reaction with Methanethiol/Triethylamine at -78 °C.2 Deprotonation with n-Butyllithium gives 2-tetrahydrofuranyl(thiomethyl)lithium [98194-88-8].1

Thiol and Disulfide Synthesis.

Reaction of 2-tetrahydrofuranyl(thiomethyl)lithium with t-Butyldimethylchlorosilane, followed by n-BuLi and a second equivalent of t-butyldimethylchlorosilane followed by hydrolysis of the adduct with Silver(I) Nitrate or Mercury(II) Chloride followed by Hydrogen Sulfide or Hydrogen Chloride gives bis(t-butyldimethylsilyl)methanethiol (t-BuMe2Si)2CHSH; 91%) (eq 1).1

Related Reagents.

2-(Methylthio)tetrahydropyran.


1. Block, E.; Aslam, M. JACS 1985, 107, 6729.
2. Brown, H. C.; Midland, M. M. JACS 1971, 93, 3291.

Eric Block

State University of New York at Albany, NY, USA



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