Estrone → HCID 131732641, compound

Temperature

0 °C

At room temperature, triethylamine (1.0 mL, 7.2 mmol, 1.2 equiv.) was added to a solution prepared by dissolving estrone (1.62 g, 6.0 mmol) in 10 mL of dichloromethane. The mixture was cooled to 0° C., and then trifluoromethanesulfonyl chloride (760 pt, 7.2 mmol, 1.2 equiv.) was added to the mixture over 3 minutes or more with stirring to effect a reaction. After 6 hours, the reaction was quenched by adding a saturated sodium hydrogen carbonate aqueous solution (10 mL) to the reaction mixture, and the reaction mixture was separated into two layers. The organic layer (dichloromethane solution) was isolated preparatively, and 20 mL of dichloromethane was added to the aqueous layer to extract the product. The above operation was repeated twice. An excess amount of anhydrous magnesium sulfate was added to the collected organic layer (dichloromethane solution), and the mixture was filtered. The solvent was evaporated under reduced pressure to obtain a concentrate including a crude product. The concentrate was subjected to silica gel flash column chromatography (eluant: hexane/ethyl acetate=5/1) to obtain estrone triflate (Rf=0.36, white solid, 1.98 g) (see below). The yield thereof was 82%.

1. customprepared
2. customa reaction
3. customthe reaction was quenched
4. additionby adding a saturated sodium hydrogen carbonate aqueous solution (10 mL) to the reaction mixture
5. customthe reaction mixture was separated into two layers
6. customThe organic layer (dichloromethane solution) was isolated preparatively
7. extractionto extract the product
8. additionAn excess amount of anhydrous magnesium sulfate was added to the collected organic layer (dichloromethane solution)
9. filtrationthe mixture was filtered
10. customThe solvent was evaporated under reduced pressure
11. customto obtain a concentrate

ORD record

ord-c89f1aa4eec24b6e86d8ed85105266a0

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993777B2