반응 #50783

반응 방정식

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

수율 62.0%

용매

dimethylformamide

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

출처