methyl 2-(3-hydroxy-4-methoxyphenyl)acetate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: Prepared according to the procedure described in Example 6, Step 2, using the following starting materials: (3-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester and 5-bromo-2-fluorobenzaldehyde. Prepared

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Hydroxy-4-methoxy-phenyl)-acetic acid methyl ester (1 g, 5.2 mmol), 2-fluoro-5-(trifluoromethyl)benzaldehyde (1 g, 5.2 mmol), and potassium carbonate (1.3 g, 10.4 mmol) were combined in THF (10 mL) and heated to 65° C. for 8 hours. After working-up the mixture with H2O and EtOAc, the crude material was purified by silica gel chromatography to give the desired product as a white solid (0.45 g). the crude material was purified by silica gel chromatography

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

実験手順: To a stirred solution of 3-hydroxy-4-methoxyphenyl acetic acid (24.8 g, 136 mmol) in 200 mL of MeOH was added 1 mL of H2SO4 and the reaction mixture was heated at reflux overnight. The methanol was removed by evaporation in vacuo and the residue was poured into saturated NaHCO3 solution and extracted with EtOAc (3×150 mL). Combined organic extracts were then washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to yield 23.9 g (90% yield) of 3-hydroxy-4-methoxyphenyl acetic acid methyl ester as a yellow oil. the reaction mixture was heated at reflux overnight The methanol was removed by evaporation in vacuo the residue was poured into saturated NaHCO3 solution extracted with EtOAc (3×150 mL) Combined organic extracts were then washed with brine dried over anhydrous MgSO4 filtered concentrated in vacuo

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: Prepared according to the procedure described in Example 7, Step 2, using the following starting materials: (3-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester and 5-bromo-2-fluorobenzaldehyde. Prepared

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

実験手順: Prepared according to the procedure described in Example 6, Step 2, using the following starting materials: (3-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester and 5-bromo-2-fluorobenzaldehyde. Prepared

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Hydroxy-4-methoxy-phenyl)-acetic acid methyl ester (1 g, 5.2 mmol), 2-fluoro-5-(trifluoromethyl)benzaldehyde (1 g, 5.2 mmol), and potassium carbonate (1.3 g, 10.4 mmol) were combined in THF (10 mL) and heated to 65° C. for 8 hours. After working-up the mixture with H2O and EtOAc, the crude material was purified by silica gel chromatography to give the desired product as a white solid (0.45 g). the crude material was purified by silica gel chromatography

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

実験手順: To a stirred solution of 3-hydroxy-4-methoxyphenyl acetic acid (24.8 g, 136 mmol) in 200 mL of MeOH was added 1 mL of H2SO4 and the reaction mixture was heated at reflux overnight. The methanol was removed by evaporation in vacuo and the residue was poured into saturated NaHCO3 solution and extracted with EtOAc (3×150 mL). Combined organic extracts were then washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to yield 23.9 g (90% yield) of 3-hydroxy-4-methoxyphenyl acetic acid methyl ester as a yellow oil. the reaction mixture was heated at reflux overnight The methanol was removed by evaporation in vacuo the residue was poured into saturated NaHCO3 solution extracted with EtOAc (3×150 mL) Combined organic extracts were then washed with brine dried over anhydrous MgSO4 filtered concentrated in vacuo