Ethyl Acetate → [8-(2-Methoxyethoxy)naphthalen-2-yl]methanol

Participants

Reaction Steps

1.64 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at 0° C. to a solution of 0.26 g of methyl 8-(2-methoxyethoxy)naphthalene-2-carboxylate (residue 35) in 20 ml of dichloromethane. After 3 hours, the reaction solution is admixed with 2 ml of ethyl acetate, stirred for 1 hour, then admixed with 3 ml of I M sodium potassium tartrate solution and subsequently stirred further for 1 hour. The reaction mixture is concentrated by evaporation—the residue is admixed with water and extracted with ethyl acetate (3×). The combined organic phases are washed successively with 1M HCl and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Provenance & Evidence