Reacción #1771

Ecuación de reacción

methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate

H2O

LiOH.H2O

→

4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoic acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to ambient temperature
2. 2
   OtroThe solvent was removed under reduced pressure
3. 3
   LavadoEtOAc and eluted with 50:50 hexanes
4. 4
   OtroThe solvent was removed under reduced pressure

Procedimiento

To a stirred solution of methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate (369 mg, 1.38 mmol) in THF:H2O (2.5 mL: 0.5 mL) was added LiOH.H2O (116.4 mg, 2.77 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a small plug of silca gel packed in 80:20 hexanes:EtOAc and eluted with 50:50 hexanes:EtOAc. The solvent was removed under reduced pressure to afford 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoic acid as a foam.

Fuente