2-(2-methoxyphenyl)propan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloro-5-{1-[2-(2-hydroxyethoxy)phenyl]-1-methylethylthio}aniline was prepared in a similar manner to that described in Reference Example 52 using 2-chloro-5-mercaptoaniline and 2-{2-[2-(tert-butyldimethyl silyloxy)ethoxy]phenyl}-2-propanol instead of 2-chloro-5-mercapto-4-methoxyaniline and 2-(2-methoxyphenyl)-2-propanol, respectively. To the solution of the obtained 2-chloro-5-{1-[2-(2-hydroxyethoxy)-phenyl]-1-methylethylthio}aniline (0.55 g) and imidazole (0.14 g) in N,N-dimethylformamide (3 mL) was added tert-butyldimethylsilyl chloride (0.24 g), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1) to give the title compound (0.66 g). the resulting mixture was extracted with ethyl acetate The extract was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To concentrated sulfuric acid (6 mL) was added water (6 mL) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added a solution of 2-chloro-5-mercapto-4-methoxyaniline (0.5 g) and 2-(2-methoxyphenyl)-2-propanol (0.88 g) in tetrahydrofuran (6 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1) to give the title compound (0.3 g). cooling the mixture was stirred at room temperature for 3 hours the resulting mixture was extracted with ethyl acetate The extract was washed with water a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1)