Monoperoxyphthalic acid → 2-(Phenylsulfinyl)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

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Reaction Steps

A solution of monoperphtalic acid in AcOEt (0.37 M solution; 20 ml) is added at 0° C. to a mixture of 2-(phenylthio)methyl-3, 5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (3.5 g) and NaHCO3 (3 g) in AcOEt (20 ml). After 30 minutes the mixture is filtered and the eluate is washed with 1N solution of sodium thiosulfate (2 ×10 ml), with a saturated solution of NaHCO3 (2×20 ml) and then with water (3×10 ml). The organic layer is dried on Na2SO4 and evaporated to dryness; the residue is purified by chromatography on SiO2 (hexane/AcOEt 85/15, as eluent) to give 3.5 g of 2-(phenylsulfinyl)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine, m.p. 160°-162° C.

Provenance & Evidence