Reacción #2304279

Ecuación de reacción

methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate

Intermediate 4

methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate

sodium hydroxide

→

title compound

Rendimiento 87.8%

5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylic acid

Rendimiento 87.8%

Disolventes

methyl alcohol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe resulting mixture was concentrated under reduced pressure
2. 2
   Extracciónextracted into diethyl ether (1×20 mL)
3. 3
   Extracciónextracted with ethyl acetate (2×25 mL)
4. 4
   SecadoThe organic extracts were dried (magnesium sulphate)
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate (Intermediate 4; 217 mg, 0.71 mmol) in methyl alcohol (3 mL) at room temperature was added a solution of sodium hydroxide (126 mg) in water (1 mL) and the reaction stirred for 18 hours. The resulting mixture was concentrated under reduced pressure, the residue taken up in water and extracted into diethyl ether (1×20 mL). The aqueous layer was acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×25 mL). The organic extracts were dried (magnesium sulphate) and concentrated under reduced pressure to give the title compound as a colourless powder (181 mg, 87%). Rf=0.21 (9:1, dichloromethane-methyl alcohol). LCMS Rt=4.33 minutes, m/z=291 (MH+).

Fuente