3-(chloromethyl)pentane

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

実験手順: The title compound was prepared following the methods described in example 1 and example 2 starting from (example 2 step 5) 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester replacing the method in example 2 step 6 with Mitsunobu method and 3-chloromethylpentane with 3-pentanol.

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

実験手順: The title compound was prepared following the methods described in example 1 and example 2 starting from (example 2 step 5) 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester replacing the method in example 2 step 6 with Mitsunobu method and 3-chloromethylpentane with 3-pentanol.

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester, 15. (0.2 g, 0.63 mmol) in DMF (5 mL) were added potassium carbonate 0.15 g (1.26 mmol), tetrabutylammonium iodide 0.03 g and 3-chloromethylpentane 0.15 g (1.26 mmol). The resulting mixture was heated at 150° C. in a microwave reactor. The mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuo to give 0.21 g (84%) of the methyl ester 16 as a white solid. extracted with EtOAc washed with brine (30 mL) dried (MgSO4) the volatiles were removed in vacuo

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester, 15. (0.2 g, 0.63 mmol) in DMF (5 mL) were added potassium carbonate 0.15 g (1.26 mmol), tetrabutylammonium iodide 0.03 g and 3-chloromethylpentane 0.15 g (1.26 mmol). The resulting mixture was heated at 150° C. in a microwave reactor. The mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuo to give 0.21 g (84%) of the methyl ester 16 as a white solid. extracted with EtOAc washed with brine (30 mL) dried (MgSO4) the volatiles were removed in vacuo

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 5-chloro-2-hydroxybenzaldehyde, 2.1 g (13.4 mmol) DMF (50 mL) under N2 atmosphere at RT was added 3-(chloromethyl)pentane (1.92 g 15.6 mmol), K2CO3 (4.5 g, 32.6 mmol) and tetrabutylammonium iodide (0.35 g, 0.9 mmol). The resulting mixture was stirred at 120° C. for 5 hours. The mixture was partitioned between water (80 ml) and EtOAc (80 ml). The organic layer was washed with water (80 ml) followed by brine (80 ml), dried over (Na2SO4), filtered and the volatiles were removed in vacuo. The crude product was purified on silica to yield to yield 2.83 g of 5-Chloro-2-(2-ethyl-butoxy)-benzaldehyde, 1. The mixture was partitioned between water (80 ml) and EtOAc (80 ml) The organic layer was washed with water (80 ml) dried over (Na2SO4) filtered the volatiles were removed in vacuo The crude product was purified on silica to yield

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 5-chloro-2-hydroxybenzaldehyde, 2.1 g (13.4 mmol) DMF (50 mL) under N2 atmosphere at RT was added 3-(chloromethyl)pentane (1.92 g 15.6 mmol), K2CO3 (4.5 g, 32.6 mmol) and tetrabutylammonium iodide (0.35 g, 0.9 mmol). The resulting mixture was stirred at 120° C. for 5 hours. The mixture was partitioned between water (80 ml) and EtOAc (80 ml). The organic layer was washed with water (80 ml) followed by brine (80 ml), dried over (Na2SO4), filtered and the volatiles were removed in vacuo. The crude product was purified on silica to yield to yield 2.83 g of 5-Chloro-2-(2-ethyl-butoxy)-benzaldehyde, 1. The mixture was partitioned between water (80 ml) and EtOAc (80 ml) The organic layer was washed with water (80 ml) dried over (Na2SO4) filtered the volatiles were removed in vacuo The crude product was purified on silica to yield

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 5-chloro-2-hydroxybenzaldehyde, 2.1 g (13.4 mmol) DMF (50 mL) under N2 atmosphere at RT was added 3-(chloromethyl)pentane (1.92 g 15.6 mmol), K2CO3 (4.5 g, 32.6 mmol) and tetrabutylammonium iodide (0.35 g, 0.9 mmol). The resulting mixture was stirred at 120° C. for 5 hours. The mixture was partitioned between water (80 ml) and EtOAc (80 ml). The organic layer was washed with water (80 ml) followed by brine (80 ml), dried over (Na2SO4), filtered and the volatiles were removed in vacuo. The crude product was purified on silica to yield to yield 2.83 g of 5-Chloro-2-(2-ethyl-butoxy)-benzaldehyde, 10. The mixture was partitioned between water (80 ml) and EtOAc (80 ml) The organic layer was washed with water (80 ml) dried over (Na2SO4) filtered the volatiles were removed in vacuo The crude product was purified on silica to yield

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 5-chloro-2-hydroxybenzaldehyde, 2.1 g (13.4 mmol) DMF (50 mL) under N2 atmosphere at RT was added 3-(chloromethyl)pentane (1.92 g 15.6 mmol), K2CO3 (4.5 g, 32.6 mmol) and tetrabutylammonium iodide (0.35 g, 0.9 mmol). The resulting mixture was stirred at 120° C. for 5 hours. The mixture was partitioned between water (80 ml) and EtOAc (80 ml). The organic layer was washed with water (80 ml) followed by brine (80 ml), dried over (Na2SO4), filtered and the volatiles were removed in vacuo. The crude product was purified on silica to yield to yield 2.83 g of 5-Chloro-2-(2-ethyl-butoxy)-benzaldehyde, 10. The mixture was partitioned between water (80 ml) and EtOAc (80 ml) The organic layer was washed with water (80 ml) dried over (Na2SO4) filtered the volatiles were removed in vacuo The crude product was purified on silica to yield

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

実験手順: The title compound was prepared following the methods described in example 1 and example 2 starting from (example 2 step 5) 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester replacing the method in example 2 step 6 with Mitsunobu method and 3-chloromethylpentane with 3-pentanol.

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

実験手順: The title compound was prepared following the methods described in example 1 and example 2 starting from (example 2 step 5) 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester replacing the method in example 2 step 6 with Mitsunobu method and 3-chloromethylpentane with 3-pentanol.

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester, 15. (0.2 g, 0.63 mmol) in DMF (5 mL) were added potassium carbonate 0.15 g (1.26 mmol), tetrabutylammonium iodide 0.03 g and 3-chloromethylpentane 0.15 g (1.26 mmol). The resulting mixture was heated at 150° C. in a microwave reactor. The mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuo to give 0.21 g (84%) of the methyl ester 16 as a white solid. extracted with EtOAc washed with brine (30 mL) dried (MgSO4) the volatiles were removed in vacuo

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-[1-(5-Chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester, 15. (0.2 g, 0.63 mmol) in DMF (5 mL) were added potassium carbonate 0.15 g (1.26 mmol), tetrabutylammonium iodide 0.03 g and 3-chloromethylpentane 0.15 g (1.26 mmol). The resulting mixture was heated at 150° C. in a microwave reactor. The mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles were removed in vacuo to give 0.21 g (84%) of the methyl ester 16 as a white solid. extracted with EtOAc washed with brine (30 mL) dried (MgSO4) the volatiles were removed in vacuo