Reacción #46189

Ecuación de reacción

1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-phenyl]-cyclopropanecarboxylic acid methyl ester

LiOH.H2O

→

1-(3-hydroxymethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid

Rendimiento 132.5%

Disolventes

MeOH

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroMeOH was removed by evaporation under vacuum
2. 2
   workup.ADDITIONAcOH (1 mol/L, 40 mL) and EtOAc (200 mL) were added
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with brine
5. 5
   Secadodried over anhydrous Na2SO4
6. 6
   Otroevaporated under vacuum

Procedimiento

To a solution of 1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-phenyl]-cyclopropanecarboxylic acid methyl ester (6.2 g, 18 mmol) in MeOH (75 mL) was added a solution of LiOH.H2O (1.50 g, 35.7 mmol) in water (10 mL) at 0° C. The reaction mixture was stirred overnight at 40° C. MeOH was removed by evaporation under vacuum. AcOH (1 mol/L, 40 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to provide 1-(3-hydroxymethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid (5.3 g).

Fuente