ethyl nonanoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry reaction tube under nitrogen were charged zinc dust (3.70 g, 56.6 mmol), iodine (479 mg, 1.89 mmol) and dry DMA (20 mL). The mixture was stirred at room temperature until the color of iodine disappeared. Ethyl 9-bromononanoate was added, and the mixture was stirred at 80° C. for 4 hours and then at room temperature overnight. (Completion of the zinc insertion reaction was checked by GCMS analysis of the hydrolyzed reaction mixture.) The reaction mixture was used without further treatment in the subsequent step. GCMS m/z 186 [M]+ (ethyl nonanoate). In a dry reaction tube under nitrogen at room temperature overnight

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (9.0 ml, 64.4 mmol) in 100 ml anhydrous THF was added dropwise n-butyl lithium (1.61N, 40.0 ml, 64.4 mmol) at -78° C. under argon atmosphere. The mixture was stirred at -78° C. for 30 minutes and ethyl nonanoate (10.00 g, 53.7 mmol) was added dropwise. After stirring the mixture at -78° C. for 30 minutes, a solution of methyl iodide (3.7 ml, 59.1 mmol) in HMPA (2.8 ml, 16.1 mmol) was added dropwise and the mixture was stirred at -78° C. for 3.5 hours. Saturated aqueous solution of ammonium chloride (20 ml) was added to the reaction mixture and the resulting mixture was then extracted with ether (50 ml×4). The ether layers were washed with water (50 ml) and with brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. Distillation gave yellow liquid, ethyl 2-methylnonanoate (9.6892 g, yield: 90.1%, b.p.: 63°-64° C./0.7 mmHg). The structure of this product was confirmed by the following data. After stirring the mixture at -78° C. for 30 minutes the mixture was stirred at -78° C. for 3.5 hours the resulting mixture was then extracted with ether (50 ml×4) The ether layers were washed with water (50 ml) and with brine (50 ml) dried over anhydrous sodium sulfate concentrated Distillation

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (9.0 ml, 64.4 mmol) in 100 ml anhydrous THF was added dropwise n-butyl lithium (1.61N, 40.0 ml, 64.4 mmol) at -78° C. under argon atmosphere. The mixture was stirred at -78° C. for 30 minutes and ethyl nonanoate (10.00 g, 53.7 mmol) was added dropwise. After stirring the mixture at -78° C. for 30 minutes, a solution of methyl iodide (3.7 ml, 59.1 mmol) in HMPA (2.8 ml, 16.1 mmol) was added dropwise and the mixture was stirred at -78° C. for 3.5 hours. Saturated aqueous solution of ammonium chloride (20 ml) was added to the reaction mixture and the resulting mixture was then extracted with ether (50 ml×4). The ether layers were washed with water (50 ml) and with brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. Distillation gave yellow liquid, ethyl 2-methylnonanoate (9.6892 g, yield: 90.1%, b.p.: 63°-64° C./0.7 mmHg). The structure of this product was confirmed by the following data. After stirring the mixture at -78° C. for 30 minutes the mixture was stirred at -78° C. for 3.5 hours the resulting mixture was then extracted with ether (50 ml×4) The ether layers were washed with water (50 ml) and with brine (50 ml) dried over anhydrous sodium sulfate concentrated Distillation

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry reaction tube under nitrogen were charged zinc dust (3.70 g, 56.6 mmol), iodine (479 mg, 1.89 mmol) and dry DMA (20 mL). The mixture was stirred at room temperature until the color of iodine disappeared. Ethyl 9-bromononanoate was added, and the mixture was stirred at 80° C. for 4 hours and then at room temperature overnight. (Completion of the zinc insertion reaction was checked by GCMS analysis of the hydrolyzed reaction mixture.) The reaction mixture was used without further treatment in the subsequent step. GCMS m/z 186 [M]+ (ethyl nonanoate). In a dry reaction tube under nitrogen at room temperature overnight

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (9.0 ml, 64.4 mmol) in 100 ml anhydrous THF was added dropwise n-butyl lithium (1.61N, 40.0 ml, 64.4 mmol) at -78° C. under argon atmosphere. The mixture was stirred at -78° C. for 30 minutes and ethyl nonanoate (10.00 g, 53.7 mmol) was added dropwise. After stirring the mixture at -78° C. for 30 minutes, a solution of methyl iodide (3.7 ml, 59.1 mmol) in HMPA (2.8 ml, 16.1 mmol) was added dropwise and the mixture was stirred at -78° C. for 3.5 hours. Saturated aqueous solution of ammonium chloride (20 ml) was added to the reaction mixture and the resulting mixture was then extracted with ether (50 ml×4). The ether layers were washed with water (50 ml) and with brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. Distillation gave yellow liquid, ethyl 2-methylnonanoate (9.6892 g, yield: 90.1%, b.p.: 63°-64° C./0.7 mmHg). The structure of this product was confirmed by the following data. After stirring the mixture at -78° C. for 30 minutes the mixture was stirred at -78° C. for 3.5 hours the resulting mixture was then extracted with ether (50 ml×4) The ether layers were washed with water (50 ml) and with brine (50 ml) dried over anhydrous sodium sulfate concentrated Distillation