5-propylfuran-2-carbaldehyde

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

Procedure: To a solution of trimethylphosphonoacetate (12.34 g; 61.6 mmol) in 500 mL of THF cooled to -78° C. under nitrogen with stirring, 136 mL (61.6 mmol) of 0.5M potassium bis(trimethylsilyl)amide was added dropwise over a 1/2 h period. The reaction mixture was stirred continuously at -78° C. for 1 hr. To the mixture was added 8.5 g (61.6 mmol) of 5-propyl-2-furancarboxaldehyde and 3 mL of THF over a 10 min period with stirring. After 1 h, stirring was stopped and the reaction mixture was allowed to warm to room temperature over a 2 h period. The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring, and water was added to dissolve the precipitated salts into solution. The THF/aqueous solution was washed with ether (200 mL), and the aqueous layer was washed again with 100 mL of ether. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield 10.95 g (87.9%) of methyl 3-(5-propyl-2-furanyl)prop-2-enoate. The reaction mixture was stirred continuously at -78° C. for 1 hr with stirring stirring The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring water was added to dissolve the precipitated salts into solution The THF/aqueous solution was washed with ether (200 mL) the aqueous layer was washed again with 100 mL of ether The combined organic layer was washed with brine dried over anhydrous magnesium sulfate filtered concentrated in vacuo

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

Procedure: To a solution of 13.04 g (0.118 mol) of 2-propylfuran in 800 mL of ether cooled at 0° C. with stirring under nitrogen was added dropwise 52 mL (0.130 mol) of 2.5 M n-butyllithium. The reaction mixture was allowed to warm to room temperature and then refluxed for 40 min. The reaction mixture was cooled to -60° C. 10.1 mL (0.130 mol) of DMF in 10 mL of ether was added, and the resulting mixture was stirred at -60° C. for 45 min, and warmed to room temperature. The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride, diluted with water to form a clear aqueous layer, and the organic layer was washed with water, and brine. The organic layer was dried over anhydrous magnesium sulfate, treated with a small amount of a charcoal, filtered, and concentrated to yield 13.95 g of a crude oil. The kughelrohr distillation of this oil (75°-105° C.) afforded 10.5 g (64.5 %) of 5-propyl-2-furancarboxaldehyde. refluxed for 40 min The reaction mixture was cooled to -60° C the resulting mixture was stirred at -60° C. for 45 min warmed to room temperature The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride diluted with water to form a clear aqueous layer the organic layer was washed with water, and brine The organic layer was dried over anhydrous magnesium sulfate treated with a small amount of a charcoal filtered concentrated to yield 13.95 g of a crude oil The kughelrohr distillation of this oil (75°-105° C.)

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

Procedure: To a solution of 13.04 g (0.118 mol) of 2-propylfuran in 800 mL of ether cooled at 0° C. with stirring under nitrogen was added dropwise 52 mL (0.130 mol) of 2.5 M n-butyllithium. The reaction mixture was allowed to warm to room temperature and then refluxed for 40 min. The reaction mixture was cooled to -60° C. 10.1 mL (0.130 mol) of DMF in 10 mL of ether was added, and the resulting mixture was stirred at -60° C. for 45 min, and warmed to room temperature. The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride, diluted with water to form a clear aqueous layer, and the organic layer was washed with water, and brine. The organic layer was dried over anhydrous magnesium sulfate, treated with a small amount of a charcoal, filtered, and concentrated to yield 13.95 g of a crude oil. The kughelrohr distillation of this oil (75°-105° C.) afforded 10.5 g (64.5 %) of 5-propyl-2-furancarboxaldehyde. refluxed for 40 min The reaction mixture was cooled to -60° C the resulting mixture was stirred at -60° C. for 45 min warmed to room temperature The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride diluted with water to form a clear aqueous layer the organic layer was washed with water, and brine The organic layer was dried over anhydrous magnesium sulfate treated with a small amount of a charcoal filtered concentrated to yield 13.95 g of a crude oil The kughelrohr distillation of this oil (75°-105° C.)

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

Procedure: To a solution of trimethylphosphonoacetate (12.34 g ; 61.6 mmol) in 500 mL of THF cooled to -78° C. under nitrogen with stirring, 136 mL (61.6 mmol) of 0.5M potassium bis(trimethylsilyl)amide was added dropwise over a 1/2 h period. The reaction mixture was stirred continuously at -78° C. for 1 hr. To the mixture was added 8.5 g (61.6 mmol) of 5-propyl-2-furancarboxaldehyde and 3 mL of THF over a 10 min period with stirring. After 1 h, stirring was stopped and the reaction mixture was allowed to warm to room temperature over a 2 h period. The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring, and water was added to dissolve the precipitated salts into solution. The THF/agueous solution was washed with ether (200 mL), and the aqueous layer was washed again with 100 mL of ether. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield 10.95 g (87.9%) of methyl 3-(5-propyl-2-furanyl)prop-2-enoate. The reaction mixture was stirred continuously at -78° C. for 1 hr with stirring stirring The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring water was added to dissolve the precipitated salts into solution The THF/agueous solution was washed with ether (200 mL) the aqueous layer was washed again with 100 mL of ether The combined organic layer was washed with brine dried over anhydrous magnesium sulfate filtered concentrated in vacuo

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

Procedure: To a solution of 13.04 g (0.118 mol) of 2-propylfuran in 800 mL of ether cooled at 0° C. with stirring under nitrogen was added dropwise 52 mL (0.130 mol) of 2.5M n-butyllithium. The reaction mixture was allowed to warm to room temperature and then refluxed for 40 min. The reaction mixture was cooled to -60° C., 10.1 mL (0.130 mol) of DMF in 10 mL of ether was added, and the resulting mixture was stirred at -60° C. for 45 min, and warmed to room temperature. The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride, diluted with water to form a clear aqueous layer, and the organic layer was washed with water, and brine. The organic layer was dried over anhydrous magnesium sulfate, treated with a small amount of a charcoal, filtered, and concentrated to yield 13.95 g of a crude oil. The kughelrohr distillation of this oil (75°-105° C.) afforded 10.5 g (64.5%) of 5-propyl-2-furancarboxaldehyde. refluxed for 40 min The reaction mixture was cooled to -60° C. the resulting mixture was stirred at -60° C. for 45 min warmed to room temperature The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride diluted with water to form a clear aqueous layer the organic layer was washed with water, and brine The organic layer was dried over anhydrous magnesium sulfate treated with a small amount of a charcoal filtered concentrated to yield 13.95 g of a crude oil The kughelrohr distillation of this oil (75°-105° C.)

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

Procedure: To a solution of trimethylphosphonoacetate (12.34 g; 61.6 mmol) in 500 mL of THF cooled to -78° C. under nitrogen with stirring, 136 mL (61.6 mmol) of 0.5M potassium bis(trimethylsilyl)amide was added dropwise over a 1/2 h period. The reaction mixture was stirred continuously at -78° C. for 1 hr. To the mixture was added 8.5 g (61.6 mmol) of 5-propyl-2-furancarboxaldehyde and 3 mL of THF over a 10 min period with stirring. After 1 h, stirring was stopped and the reaction mixture was allowed to warm to room temperature over a 2 h period. The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring, and water was added to dissolve the precipitated salts into solution. The THF/aqueous solution was washed with ether (200 mL), and the aqueous layer was washed again with 100 mL of ether. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield 10.95 g (87.9%) of methyl 3-(5-propyl-2-furanyl)prop-2-enoate. The reaction mixture was stirred continuously at -78° C. for 1 hr with stirring stirring The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring water was added to dissolve the precipitated salts into solution The THF/aqueous solution was washed with ether (200 mL) the aqueous layer was washed again with 100 mL of ether The combined organic layer was washed with brine dried over anhydrous magnesium sulfate filtered concentrated in vacuo

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

Procedure: To a solution of 13.04 g (0.118 mol) of 2-propylfuran in 800 mL of ether cooled at 0° C. with stirring under nitrogen was added dropwise 52 mL (0.130 mol) of 2.5 M n-butyllithium. The reaction mixture was allowed to warm to room temperature and then refluxed for 40 min. The reaction mixture was cooled to -60° C. 10.1 mL (0.130 mol) of DMF in 10 mL of ether was added, and the resulting mixture was stirred at -60° C. for 45 min, and warmed to room temperature. The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride, diluted with water to form a clear aqueous layer, and the organic layer was washed with water, and brine. The organic layer was dried over anhydrous magnesium sulfate, treated with a small amount of a charcoal, filtered, and concentrated to yield 13.95 g of a crude oil. The kughelrohr distillation of this oil (75°-105° C.) afforded 10.5 g (64.5 %) of 5-propyl-2-furancarboxaldehyde. refluxed for 40 min The reaction mixture was cooled to -60° C the resulting mixture was stirred at -60° C. for 45 min warmed to room temperature The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride diluted with water to form a clear aqueous layer the organic layer was washed with water, and brine The organic layer was dried over anhydrous magnesium sulfate treated with a small amount of a charcoal filtered concentrated to yield 13.95 g of a crude oil The kughelrohr distillation of this oil (75°-105° C.)