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

HRID 2257238Notes

Reaction equation

HRID 2257238 reaction equation
[C:1]1([CH2:7][C:8]([C:21]([O:23][CH2:24][CH3:25])=[O:22])([O:14]C2CCCCO2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO>[C:1]1([CH2:7][C:8]([OH:14])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 19075760Ethyl 3-phenyl-2-ethoxycarbonyl-2-(2-tetrahydropyranyloxy)-propanoate

Product 1

HCID 15828909Ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoateYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customthe solvent is evaporated under vacuum
  2. customthe mixture is partitioned between water and AcOEt
  3. customthe organic phase is separated
  4. customdried
  5. concentrationconcentrated to small volume
  6. washby elution with 90:10 cyclohexane

Sources & evidence

ORD record
ord-be72254399284c08b91c2e00f10a7264
Source dataset
uspto-grants-1997_08
Patent number
US05656656

Reaction notes

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