反应详情

Cool a mixture of sodium hydride (585 mg, 60% dispersion in mineral oil, 14.6 mmol) in dimethylformamide (20 mL, anhydrous), with an ice bath, under a nitrogen atmosphere. Add a solution of 4-benzo[b]thiophen-3-yl-phenol (3.0 g, 13.3 mmol) in dimethylformamide (20 mL) over a period of 5 minutes. Reaction mixture has noticeable gas evolution and is a yellow mixture. Stir at room temperature for 0.5 hours and cool via an ice bath to give a yellow solution. Rapidly, add a solution of (2R)-(−)-glycidyl 3-nitrobenzenesulfonate (3.78 g, 14.6 mmol) in dimethylformamide (20 mL) and stir at 0° C. for 35 minutes. The reaction mixture is a red-orange color. Stir reaction mixture at room temperature overnight. Pour the reaction mixture into cold (0° C.) water (300 mL) and extract with ethyl acetate (3×100 mL). Combine the organic layers, wash with water (100 mL), saturated sodium chloride (100 mL), dry (MgSO4) and concentrate (in vacuo) to give a brown oil. The brown oil is purified by column chromatography (dichloromethane) to give a light green/clear, viscous oil. The oil is dried (0.5 mm Hg) at room temperature for 3 hours to give the title compound as a solid (3.19 g, 85% Yield).

1. temperatureCool
2. customReaction mixture
3. temperaturecool via an ice bath
4. customto give a yellow solution
5. stirringstir at 0° C. for 35 minutes
6. stirringStir
7. customreaction mixture at room temperature overnight
8. extractionextract with ethyl acetate (3×100 mL)
9. washCombine the organic layers, wash with water (100 mL), saturated sodium chloride (100 mL)
10. dry with materialdry (MgSO4)
11. concentrationconcentrate (in vacuo)
12. customto give a brown oil
13. customThe brown oil is purified by column chromatography (dichloromethane)
14. customto give a light green/clear, viscous oil
15. customThe oil is dried (0.5 mm Hg) at room temperature for 3 hours