反应详情

52 ml of a hexane solution of 1.6M n-butyl lithium was dropped in an absolute ether (110 ml) solution of 19 g of 1-(t-butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methylnaphthalene and agitated for 1 hour. After ice cooling, 8.5 ml of N,N-dimethylformamide was dropped in the reaction solution and the ice bath was removed, followed by agitation for 1 hour until room temperature was reached. Iced water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography (2% ethyl acetate/hexane) to obtain 14.1 g of the captioned compound as a brown oily substance.

1. customthe ice bath was removed
2. waitfollowed by agitation for 1 hour until room temperature
3. additionIced water was added to the reaction solution
4. extractionfollowed by extraction with ethyl acetate
5. washThe resultant organic phase was washed with a saturated saline solution
6. dry with materialdried with anhydrous magnesium sulfate
7. customAfter removal of the solvent
8. distillationby distillation
9. customthe residue was purified by silica gel column chromatography (2% ethyl acetate/hexane)