反应详情

A solution of 456 mg (19 mmol) of sodium hydride (prepared from 760 mg of 60% sodium hydride in mineral oil by pentane wash) in 40 ml of dimethylformamide is treated portionwise with 4.05 g (19 mmol) of 3a,4,7,7a-tetrahydro-4,7-ethano-1,2-benzisothiazol-3(2H)-one-1,1-dioxide at 0° C. The resulting solution is added dropwise to a solution of 12.3 g (57 mmol) of 1,4-dibromobutane in 40 ml of dimethylformamide. The mixture is maintained with stirring at room temperature for 22.5 hours. The solvent is removed under high vacuum and the residue partitioned between methylene chloride and water. The combined methylene chloride extracts are washed with brine and dried over MgSO4. Filtration and removal of solvent in vacuo gives an oily solid which is triturated with ethyl ether and filtered to give 1.05 g of the title compound, mp 118°-122° C.

1. temperatureThe mixture is maintained
2. customThe solvent is removed under high vacuum
3. customthe residue partitioned between methylene chloride and water
4. washThe combined methylene chloride extracts are washed with brine
5. dry with materialdried over MgSO4
6. filtrationFiltration and removal of solvent in vacuo
7. customgives an oily solid which
8. customis triturated with ethyl ether
9. filtrationfiltered