Ethanol → HCID 19075898, compound

Participants

Reaction Steps

4.3 g of ethyl 2-(2-tetrahydropyranyloxy)-1,3-propanedioate are added to 11 ml of a Na ethoxide solution (prepared from 0.72 g of Na) under stirring, shielding from humidity, keeping the temperature at 0° to 5° C. After 1 h, a solution of 2.4 g of 3-pyridyl-methyl chloride hydrochloride in 8 ml of EtOH is dropped therein. The reaction mixture, which turns suddenly red, is kept under stirring at r.t. for 24 hours more. EtOH is evaporated off and the residue is partitioned between AcOEt and a 20% solution of monobasic potassium phosphate in water. The organic phase is separated, evaporated to dryness and the residue (about 4 g) is dissolved with 16 ml of 2N HCl , keeping r.t. for 4 hours; ethyl tartronate is removed by extraction with AcOEt. From the aqueous phases, after alkalization to pH 8-8.5, subsequent extraction with AcOEt, the usual work up of the organic extract and subsequent chromatography on silica gel, 1.8 g of ethyl 3-(pyrid-3-yl)-2-hydroxy-2-ethoxycarbonyl-propanoate are obtained, oil, I.R.: 3500, 3000, 1740, 1590 cm -1, TLC (SiO2 : one spot Rf : 0.24 eluent AcOEt), H-NMR(CDC13) δ (TMS): 1.2-1.3 t, 3.3 s, 4.15-4.3 q, 7.1-7.2 q, 7.6-7.65 m, 8.4-8.5 m.

Provenance & Evidence