Reacción #50783

Ecuación de reacción

ammonium chloride

17-(methoxymethoxy)-estra-1,3,5(10)-trien-3-ol

sodium hydride

1,3-dibromo-propane

→

3-[(3-bromopropyl)oxy]- 17-(methoxymethoxy)-estra-1,3,5(10)-triene

Rendimiento 62.0%

Disolventes

dimethylformamide

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature overnight
2. 2
   Extracciónfollowed by extraction with ethyl acetate
3. 3
   OtroThe solvent is removed under reduced pressure
4. 4
   Otrothe residue thus obtained
5. 5
   Otrois purified over column chromatography (n-hexane:ethyl acetate=2:1)

Procedimiento

A suspension of a 60 % sodium hydride (0.531 g) in tetrahydrofuran (100 ml) is cooled to 0° C., and 17-(methoxymethoxy)-estra-1,3,5(10)-trien-3-ol (3.5 g) is slowly added thereto. After addition of dimethylformamide (50 ml), the mixture is stirred at room temperature for 2 hours. To the resulting solution is added 1,3-dibromo-propane (2.68 g), and the mixture is stirred at room temperature overnight. The reaction mixture is poured into an aqueous ammonium chloride, followed by extraction with ethyl acetate. The solvent is removed under reduced pressure and the residue thus obtained is purified over column chromatography (n-hexane:ethyl acetate=2:1) to give 3-[(3-bromopropyl)oxy]- 17-(methoxymethoxy)-estra-1,3,5(10)-triene (3.0 g).

Fuente