Beilstein Journal of Organic Chemistry (Jun 2010)

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

  • Bruno Linclau,
  • Leo Leung,
  • Jean Nonnenmacher,
  • Graham Tizzard

DOI
https://doi.org/10.3762/bjoc.6.62
Journal volume & issue
Vol. 6, no. 1
p. 62

Abstract

Read online

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.

Keywords