3-(3-chlorophenyl)propanal

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: A solution of 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester (0.118 g, 0.5 mmol) and diisopropylethylamine (0.071 g, 0.55 mmol) in 10 mL MeOH was stirred at room temperature for 30 minutes and 3-(3-chloro-phenyl)-propionaldehyde (0.093 g, 0.55 mmol) was added. The mixture was stirred for 90 minutes. The reaction was cooled to 0° C., NaBH4 (0.83 mL, 5.98 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched with 1:1 NaHCO3:H2O and was washed with CH2Cl2. The CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an oil (171 mg). MS 352 (M+1). the mixture was stirred for 30 minutes The reaction was quenched with 1:1 NaHCO3 H2O and was washed with CH2Cl2 The CH2Cl2 extracts were washed with brine dried over MgSO4 filtered concentrated in vacuo

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

実験手順: A solution of 1-chloro-3-iodobenzene (9.63 g, 40.38 mmol), allyl alcohol (5.86 g, 100.96 mmol), sodium bicarbonate (8.48 g, 100.96 mmol), tetrabutylammonium chloride (11.22 g, 40.38 mmol), and Pd(OAc)2 (317 mg, 1.413 mmol) in 25 mL DMF was stirred at 50° C. for 18 h. The mixture was cooled to room temperature, diluted with water, and the aqueous solution was washed with EtOAc. The organic solution was washed with water followed by brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc) to afford the title compound as an oil (5.04 g). the aqueous solution was washed with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc)

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

実験手順: A solution of 1-chloro-3-iodobenzene (9.63 g, 40.38 mmol), allyl alcohol (5.86 g, 100.96 mmol), sodium bicarbonate (8.48 g, 100.96 mmol), tetrabutylammonium chloride (11.22 g, 40.38 mmol), and Pd(OAc)2 (317 mg, 1.413 mmol) in 25 mL DMF was stirred at 50° C. for 18 h. The mixture was cooled to room temperature, diluted with water, and the aqueous solution was washed with EtOAc. The organic solution was washed with water followed by brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc) to afford the title compound as an oil (5.04 g). the aqueous solution was washed with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc)

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

実験手順: To a 25° C. solution of 3-chlorostyrene in anhydrous CH2Cl2 ( 10.0 g, 72.15 mmol) was added a well-stirred solution of Pb(OAc)4 (35.2 g, 79.4 mmol) in trifluoroacetic acid (150 mL), dropwise. Reaction was completed within 30 minutes of the addition and after being stirred for a further 30 minutes, the mixture was poured into water, extracted with ether (3×), the combined organic layers were washed with saturated NaHCO3 solution, water, dried (MgSO4), and concentrated to a volume of about 15 mL and immediately used for the following reaction described below. Reaction was completed within 30 minutes of the addition extracted with ether (3×) the combined organic layers were washed with saturated NaHCO3 solution, water dried (MgSO4) concentrated to a volume of about 15 mL immediately used for the following reaction

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

実験手順: A solution of 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester (0.118 g, 0.5 mmol) and diisopropylethylamine (0.071 g, 0.55 mmol) in 10 mL MeOH was stirred at room temperature for 30 minutes and 3-(3-chloro-phenyl)-propionaldehyde (0.093 g, 0.55 mmol) was added. The mixture was stirred for 90 minutes. The reaction was cooled to 0° C., NaBH4 (0.83 mL, 5.98 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched with 1:1 NaHCO3:H2O and was washed with CH2Cl2. The CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an oil (171 mg). MS 352 (M+1). the mixture was stirred for 30 minutes The reaction was quenched with 1:1 NaHCO3 H2O and was washed with CH2Cl2 The CH2Cl2 extracts were washed with brine dried over MgSO4 filtered concentrated in vacuo

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

実験手順: A solution of 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester (0.118 g, 0.5 mmol) and diisopropylethylamine (0.071 g, 0.55 mmol) in 10 mL MeOH was stirred at room temperature for 30 minutes and 3-(3-chloro-phenyl)-propionaldehyde (0.093 g, 0.55 mmol) was added. The mixture was stirred for 90 minutes. The reaction was cooled to 0° C., NaBH4 (0.83 mL, 5.98 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched with 1:1 NaHCO3:H2O and was washed with CH2Cl2. The CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an oil (171 mg). MS 352 (M+1). the mixture was stirred for 30 minutes The reaction was quenched with 1:1 NaHCO3 H2O and was washed with CH2Cl2 The CH2Cl2 extracts were washed with brine dried over MgSO4 filtered concentrated in vacuo

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

実験手順: A solution of 1-chloro-3-iodobenzene (9.63 g, 40.38 mmol), allyl alcohol (5.86 g, 100.96 mmol), sodium bicarbonate (8.48 g, 100.96 mmol), tetrabutylammonium chloride (11.22 g, 40.38 mmol), and Pd(OAc)2 (317 mg, 1.413 mmol) in 25 mL DMF was stirred at 50° C. for 18 h. The mixture was cooled to room temperature, diluted with water, and the aqueous solution was washed with EtOAc. The organic solution was washed with water followed by brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc) to afford the title compound as an oil (5.04 g). the aqueous solution was washed with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc)

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: A solution of 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester (from Preparation 5, Step C, 0.118 g, 0.5 mmol) and N,N-diisopropylethylamine (0.071 g, 0.55 mmol) in 10 mL MeOH was stirred at room temperature for 30 minutes and 3-(3-chloro-phenyl)-propionaldehyde (from Preparations 3, 0.093 g, 0.55 mmol) was added. The mixture was stirred for 90 minutes. The reaction was cooled to 0° C., NaBH4 (30.3 mg, 0.801 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched with 1:1 NaHCO3:H2O and was washed with CH2Cl2. The CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an oil (171 mg). MS 352 (M+1). the mixture was stirred for 30 minutes The reaction was quenched with 1:1 NaHCO3 H2O and was washed with CH2Cl2 The CH2Cl2 extracts were washed with brine dried over MgSO4 filtered concentrated in vacuo

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

実験手順: A solution of 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester (from Preparation 5, Step C, 0.118 g, 0.5 mmol) and N,N-diisopropylethylamine (0.071 g, 0.55 mmol) in 10 mL MeOH was stirred at room temperature for 30 minutes and 3-(3-chloro-phenyl)-propionaldehyde (from Preparations 3, 0.093 g, 0.55 mmol) was added. The mixture was stirred for 90 minutes. The reaction was cooled to 0° C., NaBH4 (30.3 mg, 0.801 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched with 1:1 NaHCO3:H2O and was washed with CH2Cl2. The CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an oil (171 mg). MS 352 (M+1). the mixture was stirred for 30 minutes The reaction was quenched with 1:1 NaHCO3 H2O and was washed with CH2Cl2 The CH2Cl2 extracts were washed with brine dried over MgSO4 filtered concentrated in vacuo

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

実験手順: A solution of 1-chloro-3-iodobenzene (9.63 g, 40.38 mmol), allyl alcohol (5.86 g, 100.96 mmol), sodium bicarbonate (8.48 g, 100.96 mmol), tetrabutylammonium chloride (11.22 g, 40.38 mmol), and Pd(OAc)2 (317 mg, 1.413 mmol) in 25 mL DMF was stirred at 50° C. for 16 h. The mixture was cooled to room temperature, diluted with water, and the aqueous solution was washed with EtOAc. The organic solution was washed with water followed by brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc) to afford the title compound as an oil (5.04 g). the aqueous solution was washed with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The product was purified via flash chromatography on silica gel (9:1 hexanes:EtOAc)