반응 #456693

반응 방정식

Benzyl bromide

2-ethoxy-β-estra-3,17β-diol

2-ethoxy estra-1,3,5(10)-trien-3,17β-diol

potassium carbonate

→

oil

수율 109.7%

2-Ethoxy-3-Benzyloxy-Estra-1,3,5(10)-Triene-17β-Ol

수율 109.7%

용매

ethanol

반응 조건

후처리

1. 1
   기타The solvent was evaporated under reduced pressure
2. 2
   workup.ADDITIONthe residue was diluted with water
3. 3
   추출the mixture was extracted with ethyl acetate (3×200 mL)
4. 4
   세척The combined organic solution was washed with water (100 mL), sodium bicarbonate (120 mL), brine (100 mL)
5. 5
   건조dried over sodium sulfate
6. 6
   기타The ethyl acetate layer on evaporation under reduced pressure

실험 절차

Benzyl bromide (4.5 g, 38 mmol) was added to a suspension of 2-ethoxy-β-estra-3,17β-diol (2) (4.5 g, 13 mmol) and potassium carbonate (8.6 g, 62 mmol) in anhydrous ethanol (100 mL) under argon atmosphere at 0° C. The resulting mixture was stirred at 100±5° C. for 7-8 h. The solvent was evaporated under reduced pressure and the residue was diluted with water, and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic solution was washed with water (100 mL), sodium bicarbonate (120 mL), brine (100 mL), and dried over sodium sulfate. The ethyl acetate layer on evaporation under reduced pressure gave a viscous oil (5.8 g), which was used as such without any further purification in the next step: 1H NMR, (CDCl3) δ 7.35 (s, 5 H), 6.75 (s, 1 H) 6.65 (s, 1 H), 5.5 (s, 1 H), 4.55 (s, 2 H), 4.04 (q, J=6.4, 2 H), 3.5 (t, J=8.5 Hz, 1 H), 2.75 (m, 3 H), 2.20-1.95 (m, 6 H), 1.90-1.80 (m, 2 H), 1.75-1.5 (m, 2 H), 1.45-1.1 (m, 7 H, 0.85 (s, 1 H).

출처