Water → HCID 15097268, compound

Participants

Reaction Steps

A solution of 3.06 g of 2-hydroxymethyl-7-(2-methoxyethoxy)methoxy-1-heptanol (prepared as described in Preparation 42) dissolved in 20 ml of dimethylformamide was added dropwise to 587 mg of sodium hydride (as a 55% 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.). After stirring the reaction mixture at room temperature for 2 hours, it was poured into 300 ml of water and then extracted five times with ethyl acetate. The combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The oily residue was subjected to column chromatography through 60 g of silica gel, and 2.37 g of the title compound were obtained from the fractions eluted with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:1 by volume, as a colorless oil.

Provenance & Evidence