Reacción #1616

ord-f128083fd7554ead9f40eeecd8845c28

Ecuación de reacción

Oc1ccc(OCc2ccccc2)cc1
4-benzyloxyphenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(S)-Glycidyl-3-nitrobenzenesulphonate
Oc1ccc(OCc2ccccc2)cc1C[C@H]1CO1
title compound
Oc1ccc(OCc2ccccc2)cc1C[C@H]1CO1
(S)-Glycidyl-4-benzyloxyphenol

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas heated
  2. 2
    Temperaturaunder reflux for 15 mins
  3. 3
    Temperaturathe reaction mixture was heated
  4. 4
    Temperaturaunder reflux for 18 hours
  5. 5
    TemperaturaAfter cooling
  6. 6
    Filtraciónthe reaction mixture was filtered
  7. 7
    Otrothe solvent was evaporated
  8. 8
    OtroThe residue was partitioned between ethyl acetate and water
  9. 9
    Lavadowashed with water and brine
  10. 10
    Otrodried
  11. 11
    Otroevaporated

Procedimiento

A mixture of 4-benzyloxyphenol (2.0 g, 10 mMol) and potassium carbonate (4.14 g, 30 mMol) in acetone (50 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (2.23 g, 10 mMol) was added and the reaction mixture was heated under reflux for 18 hours. After cooling, the reaction mixture was filtered and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic fractions were combined, washed with water and brine, dried and evaporated to give the title compound as an oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726165uspto-grants-1998_03