Methyl Ethyl Ketone → HCID 53733693, compound

Participants

Reaction Conditions

Reaction Steps

At -50° C., 16.6 ml of a 1.6 molar n-butyllithium solution in hexane are introduced into a prepared mixture of 3.1 g of N,N,N',N'-tetramethylethylenediamine and 25 ml of absolute tetrahydrofuran. 6.2 g of 2-[(4,6-dimethoxy-pyrimidin-2-yl)thio]-acetic acid ethyl ester dissolved in 15 ml of tetrahydrofuran are then added dropwise thereto at a temperature of -65° C. and the mixture is stirred for 20 minutes. 2.4 ml of ethyl methyl ketone are added at a temperature below -60° C. and the reaction mixture is heated to room temperature in the course of 1 hour. Ice-water is then added to the reaction mixture which is then extracted twice with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation. Column chromatography on silica gel, eluant ethyl acetate/hexane 1:4 yields pure 2-[(4,6-dimethoxy-pyrimidin-2-yl)thio]-3-hydroxy-3-methylpentanoic acid ethyl ester in the form of a yellow oil; 1H-NMR(CDCl3): 1.36/1.40, 2s, CH3 ; 3.17/3.31, OH; 3.93, s, OCH3 ; 4.2, m, OCH2CH3 ; 4.79/4.80, 2s, CH; 5.76, s, CH; 70/30 isomeric mixture.

Provenance & Evidence