Reacción #2304278

Ecuación de reacción

methyl 5-bromo-2-furoate

hydrochloric acid

5-trimethylsilyl-2-methylphenol

Intermediate 3

5-trimethylsilyl-2-methylphenol

potassium tert-butoxide

→

title compound

Rendimiento 57.0%

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

Rendimiento 57.0%

Disolventes

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction heated
2. 2
   Temperaturaat reflux for 1.5 hours
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   Temperaturaheated at 85° C. for 18 hours
5. 5
   Temperaturato cool to room temperature
6. 6
   ExtracciónThe mixture was extracted with diethyl ether (3×30 mL)
7. 7
   Secadothe combined organic extracts were dried (magnesium sulphate)
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   Otropurified by column chromatography (SiO2; light petroleum to 95:5 light petroleum-diethyl ether)

Procedimiento

To a solution of 5-trimethylsilyl-2-methylphenol (Intermediate 3; 653 mg, 3.6 mmol) in THF was added potassium tert-butoxide (407 mg, 3.6 mmol) and the reaction heated at reflux for 1.5 hours. The resulting solution was allowed to cool to room temperature and concentrated under reduced pressure. The residue was taken up in dimethyl sulphoxide (10 mL), treated with methyl 5-bromo-2-furoate (632 mg, 3.1 mmol) and heated at 85° C. for 18 hours. The dark brown mixture was allowed to cool to room temperature, diluted with water (10 mL) and then acidified by the addition of hydrochloric acid (1 M). The mixture was extracted with diethyl ether (3×30 mL) and the combined organic extracts were dried (magnesium sulphate), concentrated under reduced pressure and purified by column chromatography (SiO2; light petroleum to 95:5 light petroleum-diethyl ether) to give the title compound as a colourless oil (534 mg, 57%). Rf=0.21 (9:1 light petroleum-diethyl ether). LCMS Rt=4.9 mins, m/z=305 (MH+).

Fuente