Water → HCID 13687912, compound

Participants

Reaction Steps

8.4 ml (66.2 mmol) of trimethylchlorosilane are added to 9.17 g (33.1 mmol) of 2-acetyl-6-(1-hydroxy-1-(3-pyridyl) methyl)naphthalene and 13.8 ml (99.3 mmol) of absolute triethylamine in 200 ml of absolute dichloromethane at 0° C., with stirring. After the mixture has stood at room temperature overnight, it is evaporated, the residue is taken up in sodium bicarbonate solution, and the solution is extracted with ethyl acetate. After drying and evaporation, the residue (12.4 g) is dissolved in 35 ml of dioxane and is added, at 0° to 10° C., to a solution of 14.2 g (0.355 mol) of sodium hydroxide in 70 ml of water, to which 5.5 ml (106.5 mmol, 17 g) of bromine have previously been added dropwise. After the mixture has stood overnight at room temperature, 10 ml of acetone are added, and the mixture is stirred for 30 minutes, extracted twice with ethyl acetate, and the aqueous phase is adjusted to pH 2 with 2 N HCl and is evaporated. The residue is then extracted by boiling with isopropanol and is evaporated. The remaining residue is taken up in 400 ml of 1 N methanolic hydrochloric acid, and the solution is allowed to stand at room temperature overnight. It is then evaporated, and the residue is taken up in sodium carbonate solution which is extracted with ethyl acetate. 4.4 g of crude product are obtained after drying and evaporation, from which 3.63 g (37%) of methyl 6-[1-hydroxy-1-(3-pyridyl) methyl]-2-naphthoate are isolated by chromatography on silica gel (ethyl acetate).

Provenance & Evidence