methyl 3-oxo-2-propanoylpentanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:2.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7.50 g (40.3 mmol) of 3-oxo-2-propionyl-pentanoic acid methyl ester were dissolved in 40 ml of MeCN and the mixture cooled to 2° C. While stirring, 13.26 g (40.3 mmol) of caesium carbonate were added in small portions and the reaction then warmed up to RT. 6.86 g=4.73 ml (40.3 mmol) of methyl trifluoromethanesulfonate were then added drop by drop between 22 and 25° C. After 90 min, the reaction mixture was poured into crashed ice and extracted twice with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 7.86 g of crude compound as yellow oil. the reaction then warmed up to RT the reaction mixture was poured extracted twice with Et2O the organic phases were washed with water dried over magnesium sulfate filtered evaporated

反応条件: temp:2.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7.50 g (40.3 mmol) of 3-oxo-2-propionyl-pentanoic acid methyl ester were dissolved in 40 ml of MeCN and the mixture cooled to 2° C. While stirring, 13.26 g (40.3 mmol) of caesium carbonate were added in small portions and the reaction then warmed up to RT. 6.86 g=4.73 ml (40.3 mmol) of methyl trifluoromethanesulfonate were then added drop by drop between 22 and 25° C. After 90 min, the reaction mixture was poured into crashed ice and extracted twice with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 7.86 g of crude compound as yellow oil. the reaction then warmed up to RT the reaction mixture was poured extracted twice with Et2O the organic phases were washed with water dried over magnesium sulfate filtered evaporated

反応条件: temp:2.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.21 g=5.02 ml (39.2 mmol) of 3-oxo-pentanoic acid methyl ester were dissolved in 30 ml of CH2Cl2, the solution was cooled to 2° C. and 3.81 g (39.2 mmol) of anhydrous magnesium chloride were added in small portions. Then, 6.21 g=6.34 ml (78.4 mmol) of pyridine were added to this suspension between 2° C. and 5° C., followed by 3.89 g=3.67 ml (41.2 mmol) of propionyl chloride. The reaction mixture was warmed up to RT and 1 hour later poured into crashed ice, acidified with HCl (25%) to pH 1-2 and extracted twice with Et2O. The organic phases were dried over magnesium sulfate, filtered and evaporated to give 7.62 g of title compound as light yellow oil. MS: 185.1 ([M−H]−). The reaction mixture was warmed up to RT and 1 hour later poured extracted twice with Et2O The organic phases were dried over magnesium sulfate filtered evaporated

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

実験手順: A solution of 7.5 g (40 mmol) of the compound of step A and 11.85 g (48 mmol) of 2,6-dichloro-4-trifluoromethylphenyl hydrazine in 50 mL of ethanol was heated at reflux for 8 hours. The ethanol was removed by evaporation and the residues were partitioned between ethyl acetate and dilute hydrogen chloride. The organic extracts were dried and evaporated to give the desired product in 43% yield as a maroon oil. 1H-NMR (CDCl3) δ1.08 (3H, t, J=7), 1.24 (3H, t, J=7), 2.22 (2H, q, J=7), 2.94 (2H, q, J=7), 3.86 (3H, s), 7.46 (2H, s). at reflux for 8 hours The ethanol was removed by evaporation the residues were partitioned between ethyl acetate and dilute hydrogen chloride The organic extracts were dried evaporated

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6.5 g (50 mmol) of methyl propionyl acetate in 100 mL of ether was treated with 1.19 g (50 mmol) of sodium hydride and the mixture was stirred for 2 hours. The mixture was then cooled to 5° C. and 6.93 g (6.51 mL. 75 mmol) of propionyl chloride was added dropwise over 5 minutes. The reaction mixture was stirred overnight at room temperature and then poured into cold water. This mixture was acidified with sulfuric acid and the product was extracted into ether, washed with water and dried. Evaporation gave the desired product, sufficiently pure for use in the following reaction, in 88% yield. 1H-NMR (CDCl3) δ1.08 (6H, t, J=7), 2.58 (4H, q. J=7), 3.66 (1H, s), 3.74 (3H, s). The reaction mixture was stirred overnight at room temperature the product was extracted into ether washed with water dried Evaporation

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6.5 g (50 mmol) of methyl propionyl acetate in 100 mL of ether was treated with 1.19 g (50 mmol) of sodium hydride and the mixture was stirred for 2 hours. The mixture was then cooled to 5° C. and 6.93 g (6.51 mL. 75 mmol) of propionyl chloride was added dropwise over 5 minutes. The reaction mixture was stirred overnight at room temperature and then poured into cold water. This mixture was acidified with sulfuric acid and the product was extracted into ether, washed with water and dried. Evaporation gave the desired product, sufficiently pure for use in the following reaction, in 88% yield. 1H-NMR (CDCl3) δ1.08 (6H, t, J=7), 2.58 (4H, q. J=7), 3.66 (1H, s), 3.74 (3H, s). The reaction mixture was stirred overnight at room temperature the product was extracted into ether washed with water dried Evaporation

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

実験手順: A solution of 7.5 g (40 mmol) of the compound of step A and 11.85 g (48 mmol) of 2,6-dichloro-4-trifluoromethylphenyl hydrazine in 50 mL of ethanol was heated at reflux for 8 hours. The ethanol was removed by evaporation and the residues were partitioned between ethyl acetate and dilute hydrogen chloride. The organic extracts were dried and evaporated to give the desired product in 43% yield as a maroon oil. 1H-NMR (CDCl3) δ1.08 (3H, t, J=7), 1.24 (3H, t, J=7), 2.22 (2H, q, J=7), 2.94 (2H, q, J=7), 3.86 (3H, s), 7.46 (2H, s). at reflux for 8 hours The ethanol was removed by evaporation the residues were partitioned between ethyl acetate and dilute hydrogen chloride The organic extracts were dried evaporated

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6.5 g (50 mmol) of methyl propionyl acetate in 100 mL of ether was treated with 1.19 g (50 mmol) of sodium hydride and the mixture was stirred for 2 hours. The mixture was then cooled to 5° C. and 6.93 g (6.51 mL. 75 mmol) of propionyl chloride was added dropwise over 5 minutes. The reaction mixture was stirred overnight at room temperature and then poured into cold water. This mixture was acidified with sulfuric acid and the product was extracted into ether, washed with water and dried. Evaporation gave the desired product, sufficiently pure for use in the following reaction, in 88% yield. 1H-NMR (CDCl3) δ1.08 (6H, t, J=7), 2.58 (4H, q, J=7), 3.66 (1H, s), 3.74 (3H, s). The reaction mixture was stirred overnight at room temperature the product was extracted into ether washed with water dried Evaporation

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: A solution of 7.5 g (40 mmol) of the compound of step A and 11.85 g (48 mmol) of 2,6-dichloro-4-trifluoromethylphenyl hydrazine in 50 mL of ethanol was heated at reflux for 8 hours. The ethanol was removed by evaporation and the residues were partitioned between ethyl acetate and dilute hydrogen chloride. The organic extracts were dried and evaporated to give the desired product in 43% yield as a maroon oil. 1H-NMR (CDCl3) δ 1.08 (3H, t, J=7), 1.24 (3H, t, J=7), 2.22 (2H, q, J=7), 2.58 (4H, q. J=7), J=7), 3.86 (3H, s), 7.46 (2H, s). at reflux for 8 hours The ethanol was removed by evaporation the residues were partitioned between ethyl acetate and dilute hydrogen chloride The organic extracts were dried evaporated

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6.5 g (50 mmol) of methyl propionyl acetate in 100 mL of ether was treated with 1.19 g (50 mmol) of sodium hydride and the mixture was stirred for 2 hours. The mixture was then cooled to 5° C. and 6.93 g (6.51 mL. 75 mmol) of propionyl chloride was added dropwise over 5 minutes. The reaction mixture was stirred overnight at room temperature and then poured into cold water. This mixture was acidified with sulfuric acid and the product was extracted into ether, washed with water and dried. Evaporation gave the desired product, sufficiently pure for use in the following reaction, in 88% yield. 1H-NMR (CDCl3) δ 1.08 (6H, t, J=7), 2.58 (4H, q, J=7), 3.66 (1H, s), 3.74 (3H, s). The reaction mixture was stirred overnight at room temperature the product was extracted into ether washed with water dried Evaporation