Reacción #1090366

Ecuación de reacción

3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylic acid

3-Acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylic acid

thionyl chloride

MeOH

triethylamine

→

63

Rendimiento 69.0%

Methyl 3-Acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylate

Rendimiento 69.0%

Disolventes

dichloroethane

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter the reaction mixture was cooled to 0° C.
2. 2
   workup.STIRRINGstirred for 1 h
3. 3
   Lavadowashed with H2O, saturated aqueous NaCl
4. 4
   Secadodried (Na2SO4)
5. 5
   FiltraciónThe desiccant was filtered
6. 6
   Otrothe solvent was evaporated at reduced pressure
7. 7
   OtroThe residue was purified by column chromatography (silica gel)

Procedimiento

To a solution of 3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylic acid (62, 1.07 g, 3.0 mmol) in dichloroethane (10 mL) was added thionyl chloride (0.28 mL, 3.9 mmol) and DMF (1 drop) at room temperature. The reaction mixture was stirred for 30 min at 80° C. After the reaction mixture was cooled to 0° C., MeOH (5.0 mL) and triethylamine (1.0 mL) were added, and stirred for 1 h. The reaction mixture was diluted with EtOAc and washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1→3:2, v/v) to afford 0.764 g of 63 (69% yield) mp: 182-183° C.

Fuente