2-propylfuran

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10–90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10–90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 2-propylfuran (3.00 g, 31.2 mmol) in THF (31 mL) at −78° C. was added n-BuLi (15.0 mL, 2.5 M, 37.4 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (2.33 mL, 46.8 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with Et2O (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.38 g (91%) of compound 501A as a bright orange oil. This material was used without further purification. HPLC: 94% at 2.91 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 137.13 [M−H2O+H]+. After cooling to 0° C. the reaction was warmed to rt stirring was continued for 19 h The reaction was then cooled to 0° C. quenched with sat. NH4Cl (20 mL) followed by extraction with Et2O (2×50 mL) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated

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.)