Reacción #361362

ord-4a53a7e9919e42328dec9c7a8d87cefc

Ecuación de reacción

[Na+].[OH-]
sodium hydroxide
CO
methanol
CCCCCCCCCCOc1cnc(-c2ccc(C(C)OC(C)=O)cc2)nc1
(-)-2-{4-(1-acetoxyethyl)phenyl}-5-decyloxypyrimidine
Cl
hydrochloric acid
CCCCCCCCCCOc1cnc(-c2ccc(C(C)O)cc2)nc1
(-)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine
Rendimiento 98.5%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto subject to reaction at 40° to 45° C. for 4 hours
  2. 2
    workup.ADDITIONwas added to the reaction mixture
  3. 3
    LavadoAfter the organic phase was washed with water
  4. 4
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Procedimiento

Into 100 ml of methanol and 50 ml of tetrahydrofuran were dissolved 15 g of the (-)-2-{4-(1-acetoxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70, and then 50 ml of 20% aqueous sodium hydroxide solution were added thereto, to subject to reaction at 40° to 45° C. for 4 hours. After completion of the reaction, 4N hydrochloric acid was added to the reaction mixture to adjust it to pH 7 to 8, and then 200 ml of toluene were added to effect extraction and separation. After the organic phase was washed with water, the solvent was distilled off under reduced pressure to obtain 13.2 g (yield: 98.5%) of (-)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05389293uspto-grants-1995_02