反应详情

A solution of 3.06 g of 2-hydroxymethyl-7-(2-methoxyethoxy)methoxy-1-heptanol (prepared as described in Preparation 80) dissolved in 20 ml of dimethylformamide was added dropwise to 587 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) dispersed in 40 ml of dimethylformamide, whilst ice-cooling (at 5° to 7° C.). The mixture was then stirred at room temperature for 1 hour, after which 1.60 ml of benzyl bromide were added dropwise, whilst ice-cooling (at 5° to 7° C.) The reaction mixture was stirred at room temperature for 2 hours, after which it was poured into 300 ml of water and then extracted five times with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting oily residue was subjected to column chromatography through 60 g of silica gel, and 2.37 g of the title compound were obtained, as a colorless oil, from the fractions eluted with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:1 by volume.

1. temperaturecooling (at 5° to 7° C.)
2. temperaturecooling (at 5° to 7° C.) The reaction mixture
3. stirringwas stirred at room temperature for 2 hours
4. extractionextracted five times with ethyl acetate
5. washThe combined extracts were washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated by evaporation under reduced pressure