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Under an argon atmosphere, 2 g (0.007 mol) of 4-[(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]-butanoic acid methyl ester in 5 ml of anhydrous dimethylformamide was added to a suspension of 0.29 g of sodium hydride in 25 ml of anhydrous dimethylformamide. The mixture was stirred at room temperature for 20 minutes and then 7.7 g of bis-(2-bromoethyl)ether was added and the mixture was stirred at room temperature for 20 hours. The solvent was removed and residual oil was purified by high pressure liquid chromatography using 25% ethyl acetate-hexane to yield 1.6 g (54%) of 4-[[8-acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester as an oil.

1. stirringthe mixture was stirred at room temperature for 20 hours
2. customThe solvent was removed
3. customresidual oil was purified by high pressure liquid chromatography