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2005
Hydroxycarboxylic acids (ether carboxylic acids) and esters
P 0280
The Efficient Synthesis of Alkoxy-esters from Hydroxy Carboxylic Acids Using
in Dimethylsulfoxide Followed by Alkylation with an Alkyl
16- 064 Dimsyllithium
Halide. — Double deprotonation of hydroxy acids by dimsyllithium in DMSO followed by treatment with alkyl halide provides the corresponding ether-esters in good
yields. No evidence of racemization at the stereogenic center of optically active acids
is observed. The generation of dimsyllithium is performed by slow addition of BuLi to
DMSO. This method is a mild alternative to stirring of NaH or LiH in DMSO. —
(PAGE, P. C. B.; CHAN, Y.; HEANEY*, H.; MCGRATH, M. J.; MORENO, E.;
Synlett 2004, 14, 2606-2608; Dep. Chem., Loughborough Univ., Loughborough,
Leicestershire LE11 3TU, UK; Eng.) — Klein
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