3-ethoxy-2-fluorophenol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 3-ethoxy-2-fluoro-phenol (6.00 g, 0.038 mol) and ethyl-2-butynoate (8.60 g, 0.077 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.80 g, 0.038 mol) slowly. After addition was complete the mixture was stirred at reflux for 7 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The crude product, (E)-3-(3-ethoxy-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester, was obtained as a brown oil (6.00 g, 58%) and used without further purification. After addition at reflux for 7 h was removed in vacuo the residue was diluted in diethyl ether washed first with 1N aqueous hydrochloric acid 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-ethoxy-2-fluoro-phenylboronic acid (10.0 g, 0.054 mol) in tetrahydrofuran (150 mL) was added glacial acetic acid (60 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 8 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 23 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated to give 3-ethoxy-2-fluoro-phenol (6.00 g, 71%) as a brown oil. was added to come to room temperature The mixture was evaporated the residue was dissolved in ethyl acetate washed with hydrochloric acid (0.5N), water and brine The organic phase was dried filtered evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 3-ethoxy-2-fluoro-phenol (6.00 g, 0.038 mol) and ethyl-2-butynoate (8.60 g, 0.077 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.80 g, 0.038 mol) slowly. After addition was complete the mixture was stirred at reflux for 7 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The crude product, (E)-3-(3-ethoxy-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester, was obtained as a brown oil (6.00 g, 58%) and used without further purification. After addition at reflux for 7 h was removed in vacuo the residue was diluted in diethyl ether washed first with 1N aqueous hydrochloric acid 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-ethoxy-2-fluoro-phenylboronic acid (10.0 g, 0.054 mol) in tetrahydrofuran (150 mL) was added glacial acetic acid (60 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 8 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 23 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated to give 3-ethoxy-2-fluoro-phenol (6.00 g, 71%) as a brown oil. was added to come to room temperature The mixture was evaporated the residue was dissolved in ethyl acetate washed with hydrochloric acid (0.5N), water and brine The organic phase was dried filtered evaporated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 3-ethoxy-2-fluoro-phenol (6.00 g, 0.038 mol) and ethyl-2-butynoate (8.60 g, 0.077 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.80 g, 0.038 mol) slowly. After addition was complete the mixture was stirred at reflux for 7 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The crude product, (E)-3-(3-ethoxy-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester, was obtained as a brown oil (6.00 g, 58%) and used without further purification. After addition at reflux for 7 h was removed in vacuo the residue was diluted in diethyl ether washed first with 1N aqueous hydrochloric acid 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-ethoxy-2-fluoro-phenylboronic acid (10.0 g, 0.054 mol) in tetrahydrofuran (150 mL) was added glacial acetic acid (60 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 8 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 23 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated to give 3-ethoxy-2-fluoro-phenol (6.00 g, 71%) as a brown oil. was added to come to room temperature The mixture was evaporated the residue was dissolved in ethyl acetate washed with hydrochloric acid (0.5N), water and brine The organic phase was dried filtered evaporated