methyl 3-(3-fluoro-5-hydroxyphenyl)propanoate

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

Procedure: To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (350 mg) in acetonitrile (25 mL) were added methyl 3-(3-fluoro-5-hydroxyphenyl)propanoate (208 mg) and cesium carbonate (1.41 g), and the mixture was heated under reflux for 15 hr. Ethyl acetate was added to the reaction mixture, and the insoluble material was filtered off. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (390 mg) as a white solid. the mixture was heated under reflux for 15 hr the insoluble material was filtered off The solvent in the filtrate was evaporated under reduced pressure the residue was purified by silica gel column chromatography (ethyl acetate/hexane)

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

Procedure: To a solution of methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate (2.60 g) in methanol (15 mL) was added 10% palladium-activated carbon (2.20 g), and the mixture was stirred for 1 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (710 mg) as a white solid. The reaction mixture was filtered the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

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

Procedure: To a solution of methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate (2.60 g) in methanol (15 mL) was added 10% palladium-activated carbon (2.20 g), and the mixture was stirred for 1 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (710 mg) as a white solid. The reaction mixture was filtered the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

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

Procedure: To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (350 mg) in acetonitrile (25 mL) were added methyl 3-(3-fluoro-5-hydroxyphenyl)propanoate (208 mg) and cesium carbonate (1.41 g), and the mixture was heated under reflux for 15 hr. Ethyl acetate was added to the reaction mixture, and the insoluble material was filtered off. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (390 mg) as a white solid. the mixture was heated under reflux for 15 hr the insoluble material was filtered off The solvent in the filtrate was evaporated under reduced pressure the residue was purified by silica gel column chromatography (ethyl acetate/hexane)

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

Procedure: To a solution of methyl 3-(3-(benzyloxy)-5-fluorophenyl)acrylate (2.60 g) in methanol (15 mL) was added 10% palladium-activated carbon (2.20 g), and the mixture was stirred for 1 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (710 mg) as a white solid. The reaction mixture was filtered the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)