Hydrochloric Acid → HCID 20100317, compound

Participants

Reaction Steps

To a solution of methyl 4-[3-(benzyloxy)phenyl]benzoate (1.2 g) in tetra hydrofuran (20 mL) was added lithium aluminum hydride (0.21 g) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes, and stirred at room temperature for 2 hours. To the reaction mixture was added ethyl acetate (10 mL), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was acidified by addition of 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethylacetate. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-2/1) to give 4-[3-(benzyloxy)-phenyl]benzyl alcohol (0.32 g). This material was dissolved in ethyl acetate (4 mL). To the solution was added triethylamine (0.20 mL). To the mixture was added methanesulfonyl chloride (0.094 mL) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. The insoluble material was removed by filtration. To the filtrate were added ethyl acetate (6 mL) and lithium bromide monohydrate (0.58 g), and the mixture was stirred at 55° C. for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=20/1) to give the title compound (0.36 g).

Provenance & Evidence