Water → 3-Methoxyestra-2,5(10)-dien-17-one

Temperature

109 °C

To a stirred solution of 106.3 g (0.52 mmol) of aluminum isopropoxide in 2000 ml of dry toluene 720 ml of cyclohexanone, 0.35 g of 2,6-ditert-butyl-4-methyl-phenol and 100 g (0.307 mol) 3-methoxy-17-hydroxy-estra-2,5(10)-diene were added, then the reaction mixture was stirred at 108-110° C. for 1 h. The reaction was followed by TLC. After completion of the reaction the mixture was cooled to 20-25° C., 200 ml of water was added and the so obtained mixture was stirred for 1 h. The precipitated aluminum hydroxide was filtered off and the filtrate was concentrated to a volume of 250 ml under reduced pressure. A mixture of 200 ml of methanol and 100 ml of water was added to this concentrated warm—about 60° C.—solution, the obtained suspension was cooled to 20-25° C. and stirred for 1 h. The precipitated crystalline product was filtered off and dried below 40° C. in vacuum to yield 76.4 g (87%) of the title compound.

1. customAfter completion of the reaction the mixture
2. temperaturewas cooled to 20-25° C.
3. stirringthe so obtained mixture was stirred for 1 h
4. filtrationThe precipitated aluminum hydroxide was filtered off
5. concentrationthe filtrate was concentrated to a volume of 250 ml under reduced pressure
6. additionA mixture of 200 ml of methanol and 100 ml of water
7. additionwas added to this concentrated
8. temperaturewarm—about 60° C.—solution
9. temperaturethe obtained suspension was cooled to 20-25° C.
10. stirringstirred for 1 h
11. filtrationThe precipitated crystalline product was filtered off
12. customdried below 40° C. in vacuum

ORD record

ord-96227a8b2b07442782f7117f5cad8a6e

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314145B2