Reacción #941719

Ecuación de reacción

(3-Hydroxy-phenyl)-acetic acid methyl ester

N,N-dimethyl thiocarbamoyl chloride

triethylamine

→

title compound

(3-Dimethylthiocarbamoyloxy-phenyl)-acetic acid methyl ester

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux 18 hr
2. 2
   ConcentraciónThe mixture is concentrated
3. 3
   SecadoThe combined organic extracts are dried over anhydrous magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   Otropurified via silica chromatography
7. 7
   Lavadoeluting the product with dichloromethane

Procedimiento

A mixture of (3-Hydroxy-phenyl)-acetic acid methyl ester (5.5 g, 33.1 mmol), N,N-dimethyl thiocarbamoyl chloride (5.11 g, 41.38 mmol), triethylamine (9.2 mL, 66.2 mmol), N,N-dimethylamino pyridine (0.4 g, 3.31 mmol) and dioxane (50 mL) is stirred at reflux 18 hr. The mixture is concentrated, partioned between 1M aqueous hydrochloric acid (200 mL) and ethyl acetate (3×75 mL). The combined organic extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting the product with dichloromethane to afford the title compound as a brown oil, 6.8 g, 81%. MS M++1 254. The structure is confirmed by 1H NMR spectroscopy.

Fuente