Ethyl 3-phenyl-2-ethoxycarbonyl-2-(2-tetrahydropyranyloxy)-propanoate → Ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoate

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Reaction Steps

25 mg of pTS acid are added to a solution of ethyl 3-phenyl-2-ethoxycarbonyl-2-(2-tetrahydropyranyloxy)-propanoate (6 g) in EtOH (25 ml). After 12 hours at r.t., the solvent is evaporated under vacuum, the mixture is partitioned between water and AcOEt; the organic phase is separated, dried, concentrated to small volume. The residue is adsorbed on SiO2 (40 g); by elution with 90:10 cyclohexane:AcOEt, 4.3 g of ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoate, oil, are obtained. I.R.: 3500, 3000, 1740, 1600 cm-1 ; HNMR (CDCl3) δ (TMS): 1.2-1.35 t, 3.35 s, 3.15 s, 4.2-4.3 q, 7.25 s.

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