Hydrochloric Acid → HCID 86752725, compound

To a suspension of magnesium (0.110 g 4.5 mmol) in THF (1.0 mL) was added bromoethane (0.50 mL, 6.6 mmol) dissolved in THF (1.0 mL) at room temperature. 3-Hydroxy-17β-methoxyestra-1,3,5(10)-triene (41, 0.258 g, 0.90 mmol; synthesized by the method of Coombs et al., Steroids 6(6):841-844 (1965)), dissolved in THF (3.0 mL) was added to the reaction mixture, and stirring continued for 30 min. The solvent was removed at reduced pressure, and to the residue were added benzene (10 mL, hexamethylphosphoric triamide (0.40 mL, 2.1 mmol) and paraformaldehyde (0.370 g). Stirring was continued for 2 h at 80° C. After the reaction mixture was cooled to room temperature, 5N HCl (5.0 mL) was added and the mixture extracted with EtOAc. The combined organic layers were washed with H2O, then with saturated aqueous NaCl, and 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:AcOEt (10:1→8:1, v/v) to afford 0.221 g of 42 (78% yield), m.p. 120°-121° C.

1. additionwas added to the reaction mixture
2. customThe solvent was removed at reduced pressure
3. stirringStirring
4. waitwas continued for 2 h at 80° C
5. extractionthe mixture extracted with EtOAc
6. washThe combined organic layers were washed with H2O
7. dry with materialwith saturated aqueous NaCl, and dried (Na2SO4)
8. filtrationThe desiccant was filtered
9. customthe solvent was evaporated at reduced pressure
10. customThe residue was purified by column chromatography (silica gel)

ORD record

ord-6babae78deb14875bfa4874647bc1932

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763432