methyl 3-(4-chlorophenyl)propanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: BuLi (5.2 mL, 1.6M in hexanes) was added to a 0° C. solution of diisopropylamine (0.91 g, 9.0 mmol) in THF (40 mL). The reaction mixture was then stirred at 0° C. for 30 minutes, and then cooled to −78° C. A solution of methyl 3-(4-chlorophenyl)propanoate (1.5 g, 7.5 mmol) in THF (8 mL) was added slowly, and the reaction mixture was stirred at −78° C. for 40 minutes. A solution tert-butyl 2-bromoacetate (4.4 g, 22.7 mmol) in THF (5 mL) was then added. The reaction was then stirred for 30 minutes at −78° C. and then warmed to room temperature and stirred overnight. The reaction was then quenched with saturated NH4Cl and concentrated to remove THF. The reaction was then extracted with EtOAc, and the combined extracts were dried (Na2SO4), filtered, concentrated, and dried in vacuo to give 4-tert-butyl 1-methyl 2-(4-chlorobenzyl)succinate (1.91 g, 81%) as an oil. cooled to −78° C the reaction mixture was stirred at −78° C. for 40 minutes The reaction was then stirred for 30 minutes at −78° C. warmed to room temperature stirred overnight The reaction was then quenched with saturated NH4Cl concentrated to remove THF The reaction was then extracted with EtOAc the combined extracts were dried (Na2SO4) filtered concentrated dried in vacuo

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

実験手順: Neat SOCl2 (25.7 g, 216.7 mmol) was added dropwise to a −60° C. solution of MeOH (100 mL). Upon completion of the addition, 3-(4-chlorophenyl)propanoic acid (10.0 g, 54.1 mmol) was added in several portions. Upon completion of the addition, the cooling bath was removed, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (100 mL), washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to give methyl 3-(4-chlorophenyl)propanoate as an oil (10.48 g, 97%). was added in several portions Upon completion of the addition the cooling bath was removed The reaction was then concentrated to dryness the resulting residue was dissolved in DCM (100 mL) washed with saturated NaHCO3 dried (MgSO4) filtered concentrated

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 solution of 3-(4-chlorophenyl)propanoic acid (commercially available from Maybridge) (14.5 g, 77.1 mmol) in methanol (400 ml) was added acetyl chloride (50 ml) and the reaction mixture was refluxed for 20 h. After this time the reaction mixture was left to cool before being concentrated under reduced pressure. The residue was then dissolved in DCM (200 ml) and washed with 1 M sodium hydroxide solution (100 ml). The organic layer was dried with magnesium sulphate and concentrated in vacuo to give the title product as a brown oil (15.7 g, 77 mmol, 100%); 1HNMR (400 MHz, CDCl3) δ: 2.55 (t, 2H), 2.9 (t, 2H), 3.6 (s, 3H), 7.1 (d, 2H), 7.2 (d, 2H). the reaction mixture was refluxed for 20 h After this time the reaction mixture was left to cool before being concentrated under reduced pressure The residue was then dissolved in DCM (200 ml) washed with 1 M sodium hydroxide solution (100 ml) The organic layer was dried with magnesium sulphate concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: BuLi (5.2 mL, 1.6M in hexanes) was added to a 0° C. solution of diisopropylamine (0.91 g, 9.0 mmol) in THF (40 mL). The reaction mixture was then stirred at 0° C. for 30 minutes, and then cooled to −78° C. A solution of methyl 3-(4-chlorophenyl)propanoate (1.5 g, 7.5 mmol) in THF (8 mL) was added slowly, and the reaction mixture was stirred at −78° C. for 40 minutes. A solution tert-butyl 2-bromoacetate (4.4 g, 22.7 mmol) in THF (5 mL) was then added. The reaction was then stirred for 30 minutes at −78° C. and then warmed to room temperature and stirred overnight. The reaction was then quenched with saturated NH4Cl and concentrated to remove THF. The reaction was then extracted with EtOAc, and the combined extracts were dried (Na2SO4), filtered, concentrated, and dried in vacuo to give 4-tert-butyl 1-methyl 2-(4-chlorobenzyl)succinate (1.91 g, 81%) as an oil. cooled to −78° C the reaction mixture was stirred at −78° C. for 40 minutes The reaction was then stirred for 30 minutes at −78° C. warmed to room temperature stirred overnight The reaction was then quenched with saturated NH4Cl concentrated to remove THF The reaction was then extracted with EtOAc the combined extracts were dried (Na2SO4) filtered concentrated dried in vacuo

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

実験手順: Neat SOCl2 (25.7 g, 216.7 mmol) was added dropwise to a −60° C. solution of MeOH (100 mL). Upon completion of the addition, 3-(4-chlorophenyl)propanoic acid (10.0 g, 54.1 mmol) was added in several portions. Upon completion of the addition, the cooling bath was removed, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (100 mL), washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to give methyl 3-(4-chlorophenyl)propanoate as an oil (10.48 g, 97%). was added in several portions Upon completion of the addition the cooling bath was removed The reaction was then concentrated to dryness the resulting residue was dissolved in DCM (100 mL) washed with saturated NaHCO3 dried (MgSO4) filtered concentrated

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-(4-chlorophenyl)propanoic acid (commercially available from Maybridge) (14.5 g, 77.1 mmol) in methanol (400 ml) was added acetyl chloride (50 ml) and the reaction mixture was refluxed for 20 h. After this time the reaction mixture was left to cool before being concentrated under reduced pressure. The residue was then dissolved in DCM (200 ml) and washed with 1M sodium hydroxide solution (100 ml). The organic layer was dried with magnesium sulphate and concentrated in vacuo to give the title product as a brown oil (15.7 g, 77 mmol, 100%); 1HNMR (400 MHz, CDCl3) δ: 2.55 (t, 2H), 2.9 (t, 2H), 3.6 (s, 3H), 7.1 (d, 2H), 7.2 (d, 2H). the reaction mixture was refluxed for 20 h After this time the reaction mixture was left to cool before being concentrated under reduced pressure The residue was then dissolved in DCM (200 ml) washed with 1M sodium hydroxide solution (100 ml) The organic layer was dried with magnesium sulphate concentrated in vacuo

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-(4-chlorophenyl)propanoic acid (commercially available from Maybridge) (14.5 g, 77.1 mmol) in methanol (400 ml) was added acetyl chloride (50 ml) and the reaction mixture was refluxed for 20 h. After this time the reaction mixture was left to cool before being concentrated under reduced pressure. The residue was then dissolved in DCM (200 ml) and washed with 1M sodium hydroxide solution (100 ml). The organic layer was dried with magnesium sulphate and concentrated in vacuo to give the title product as a brown oil (15.7 g, 77 mmol, 100%); 1HNMR (400 MHz, CDCl3) δ: 2.55 (t, 2H), 2.9 (t, 2H), 3.6 (s, 3H), 7.1 (d, 2H), 7.2 (d, 2H). the reaction mixture was refluxed for 20 h After this time the reaction mixture was left to cool before being concentrated under reduced pressure The residue was then dissolved in DCM (200 ml) washed with 1M sodium hydroxide solution (100 ml) The organic layer was dried with magnesium sulphate concentrated in vacuo

反応条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of methyl 3-(4-chlorophenyl)-2,2dimethoxypropionate (6.09 g) and formic acid (27 ml) was heated at 65 to 70° C. for 4 hours with stirring. The reaction mixture was cooled and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(4-chlorophenyl)propionate. The reaction mixture was cooled extracted with methylene chloride The extract was washed with water dried over magnesium sulfate evaporated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: BuLi (5.2 mL, 1.6M in hexanes) was added to a 0° C. solution of diisopropylamine (0.91 g, 9.0 mmol) in THF (40 mL). The reaction mixture was then stirred at 0° C. for 30 minutes, and then cooled to −78° C. A solution of methyl 3-(4-chlorophenyl)propanoate (1.5 g, 7.5 mmol) in THF (8 mL) was added slowly, and the reaction mixture was stirred at −78° C. for 40 minutes. A solution tert-butyl 2-bromoacetate (4.4 g, 22.7 mmol) in THF (5 mL) was then added. The reaction was then stirred for 30 minutes at −78° C. and then warmed to room temperature and stirred overnight. The reaction was then quenched with saturated NH4Cl and concentrated to remove THF. The reaction was then extracted with EtOAc, and the combined extracts were dried (Na2SO4), filtered, concentrated, and dried in vacuo to give 4-tert-butyl 1-methyl 2-(4-chlorobenzyl)succinate (1.91 g, 81%) as an oil. cooled to −78° C the reaction mixture was stirred at −78° C. for 40 minutes The reaction was then stirred for 30 minutes at −78° C. warmed to room temperature stirred overnight The reaction was then quenched with saturated NH4Cl concentrated to remove THF The reaction was then extracted with EtOAc the combined extracts were dried (Na2SO4) filtered concentrated dried in vacuo

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

実験手順: Neat SOCl2 (25.7 g, 216.7 mmol) was added dropwise to a −60° C. solution of MeOH (100 mL). Upon completion of the addition, 3-(4-chlorophenyl)propanoic acid (10.0 g, 54.1 mmol) was added in several portions. Upon completion of the addition, the cooling bath was removed, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (100 mL), washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to give methyl 3-(4-chlorophenyl)propanoate as an oil (10.48 g, 97%). was added in several portions Upon completion of the addition the cooling bath was removed The reaction was then concentrated to dryness the resulting residue was dissolved in DCM (100 mL) washed with saturated NaHCO3 dried (MgSO4) filtered concentrated