Reaktion #738685

Reaktionsgleichung

hydrochloric acid

magnesium

product

[(9-bromononyl)oxy]dimethyl [(1,1-dimethyl)ethyl]silane

sodium bicarbonate

10-epoxy estr-9(11)-ene-17-one

→

expected product

11beta-(9-hydroxynonyl)estra-4,9-diene-3,17-dione

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis cooled down to 0°/+2° C
2. 2
   workup.ADDITIONis added
3. 3
   workup.WAITagitation is carried out for 45 minutes
4. 4
   workup.WAITagitation is carried out for 2 hours at ambient temperature
5. 5
   Extraktionfollowed by extraction with ethyl acetate
6. 6
   Waschenwashing with salt water
7. 7
   Sonstigedrying
8. 8
   Sonstigeevaporating the solvent

Vorschrift

5.2 cm3 of a solution of magnesium compound (0.42 M/l) prepared from the product obtained in Stage A and 2.3 cm3 of tetrahydrofuran is cooled down to 0°/+2° C. 30 mg of copper chloride is added, agitation is carried out for 30 minutes, followed by cooling down to −30° C. and 330 mg of 3-ethylenedioxy 5 (10-epoxy estr-9(11)-ene-17-one dissolved in 2 cm3 of tetrahydrofuran is added and agitation is carried out for 45 minutes. 6 cm3 of 2M hydrochloric acid is added and agitation is carried out for 2 hours at ambient temperature. The reaction medium is poured into a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate, washing with salt water, drying and evaporating the solvent. After chromatographing the residue on silica (eluant: ethyl acetate-cyclohexane 6-4), 192 mg of expected product is obtained.

Quelle