反应详情

To the THF solution (1000 ml) of 2-bromo-5-methoxy-benzoic acid methyl ester (20 g, 81.6 mmol), the THF suspension (50 ml) of LAH (4.07 g, 102 mmol) was added under ice cooling. The mixture was stirred for 30 min under ice cooling. The reaction solution was partitioned between saturated aqueous solution of Na2SO4 and ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residues were dissolved in DCM (200 ml), and added with TEA (12.51 ml, 89.76 mmol) and MsCl (6.63 ml, 85.68 mmol) under ice cooling, followed by stirring overnight at room temperature. The reaction mixture was diluted with DCM, and washed in order with 10% aqueous solution of citric acid, saturated aqueous solution of NaHCO3 and saturated brine. The residues obtained after concentration under reduced pressure were dissolved in DMF (100 ml), and added with the DMF (500 ml) solution of NaCN (40 g, 81.6 mmol) under ice cooling. After stirring for 2 hrs under ice cooling, the reaction mixture was extracted with ether, washed with saturated brine and dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column (hexane:ethyl acetate=10:1) to obtain the title compound (12.1 g, 67%).

1. customThe reaction solution was partitioned between saturated aqueous solution of Na2SO4 and ethyl acetate
2. washThe organic layer was washed with saturated brine
3. concentrationconcentrated under reduced pressure
4. dissolutionThe resulting residues were dissolved in DCM (200 ml)
5. stirringby stirring overnight at room temperature
6. washwashed in order with 10% aqueous solution of citric acid, saturated aqueous solution of NaHCO3 and saturated brine
7. customThe residues obtained
8. concentrationafter concentration under reduced pressure
9. dissolutionwere dissolved in DMF (100 ml)
10. stirringAfter stirring for 2 hrs under ice cooling
11. extractionthe reaction mixture was extracted with ether
12. washwashed with saturated brine
13. dry with materialdried over magnesium sulfate
14. customThe residues obtained
15. concentrationafter concentration under reduced pressure
16. customwere purified by silica gel column (hexane:ethyl acetate=10:1)