Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane.

Beilstein Journal of Organic Chemistry
Bruno LinclauGraham Tizzard

Abstract

A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed.

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Citations

Jul 19, 2018·Beilstein Journal of Organic Chemistry·Robert SzperaBruno Linclau
Sep 3, 2013·Organic & Biomolecular Chemistry·Laize A F AndradeMatheus P Freitas

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Methods Mentioned

BETA
X-ray
NMR
column chromatography

Software Mentioned

SHELXL
SADABS
DENZO
COLLECT
DAST
97
SHELXS

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