反应详情

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 0.83 ml, 1.33 mmol) was added dropwise to a solution of 2-(4-bromonaphtalen-2-ylmethyl)-5-ethylbenzo-[b]thiophene (460 mg, 1.21 mmol) in THF (15 ml) at −78° C. The reaction mixture was stirred at the same temperature for five minutes and to this solution, a solution of 3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-pyran-2-one (844 mg, 1.57 mmol) in THF (5 ml) was added dropwise. The reaction solution was stirred at −78° C. for five minutes and a saturated ammonium chloride aqueous solution was added to stop the reaction. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)] to obtain the title compound (1.06 mg, 100%).

1. stirringThe reaction solution was stirred at −78° C. for five minutes
2. customthe reaction
3. extractionThe reaction mixture was extracted with ethyl acetate
4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
5. dry with materialdried (anhydrous magnesium sulfate)
6. distillationthe solvent was distilled under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)]