反応 #50783

反応方程式

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

収率 62.0%

溶媒

dimethylformamide

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature overnight
2. 2
   抽出followed by extraction with ethyl acetate
3. 3
   その他The solvent is removed under reduced pressure
4. 4
   その他the residue thus obtained
5. 5
   その他is purified over column chromatography (n-hexane:ethyl acetate=2:1)

実験手順

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).

出典