Process for the production of threo-4-alkoxy-5- (arylhydroxymeth

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D30732

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active

052005313

ABSTRACT:
Threo-4-alkoxy-5-(arylhydroxymethyl)-2(5H)-furanones are obtained by condensation of 4-alkoxy-2(5H)-furanones with benzaldehydes in the presence of lithium hydroxide without contamination by the corresponding erythro stereoisomers. The condensation is preferably performed in aqueous acetonitrile and the product is precipitated from the alkaline reaction mixture by the addition of water. The products that can be produced according to the process of the invention are known pharmaceutical active ingredients with anticonvulsive or antiepileptic action.

REFERENCES:
patent: 4855320 (1989-08-01), Chatterjee et al.
Pelter et al., Tetrahedron Letters, No. 18, (1970, pp. 1627-1630).
Fieser, "Fieser and Fieser's Reagents For Organic Synthesis", vol. 8, (1980), p. 268.
Pelter et al., J. Chem. Soc. Perkin Trans. I, (1987), pp. 717 to 742.

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