反应详情

13.7 g of t-butylchlorodimethylsilane was added to an N,N-dimethylaminopyridine (100 ml) solution of 14 g of 1-hydroxymethyl-4-methoxymethoxy-5-methylnaphthalene, 6.64 g of imidazole, and 0.4 g of 4-dimethylaminopyridine and agitated at room temperature overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. Thereafter, the resultant organic phase was washed with water and then with a saturated saline solution. After drying with anhydrous magnesium sulfate, the solvent was distilled off and the residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to obtain 19 g of the captioned compound as a light brown oily substance.

1. extractionfollowed by extraction with ethyl acetate
2. washThereafter, the resultant organic phase was washed with water
3. dry with materialAfter drying with anhydrous magnesium sulfate
4. distillationthe solvent was distilled off
5. customthe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)