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With pyridine; trifluoroacetic anhydride In 1,4-dioxane; chloroform; ethyl acetate
Preparation c-129 Tetrahydro-furan-2-carbonitrile Trifluoroacetic anhydride (1.55 g, 7.38 mmol) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0° C.) of tetrahydro-furan-2-carboxylic acid amide (0.77 g, 6.71 mmol) and pyridine (1.06 g, 13.42 mmol) in anhydrous 1,4-dioxane (10 mL). The addition of trifluoroacetic anhydride was monitored to keep the internal temperature below 5° C. and was completed after 20 minutes. The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours. Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL). The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated in vacuo to give the crude product. The residue was purified by flash column chromatography (hexanes to 25percent ethyl acetate/hexanes) to afford the title compound (0.51 g, 62percent) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 4.70 (1H, m), 3.96 (2H, m), 2.24 (2H, m), 2.08 (2H, m).
62%
With pyridine; trifluoroacetic anhydride In 1,4-dioxane at 5 - 20℃; for 3.33333 h;
Trifluoroacetic anhydride (1. 55 g, 7. 38 MMOL) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0 °C) of tetrahydro-furan-2- carboxylic acid amide (0. 77 g, 6. 71 MMOL) and pyridine (1. 06 g, 13. 42 MMOL) in anhydrous 1, 4-dioxane (10 mL). The addition of TRIFLUOROACETIC anhydride was monitored to keep the internal temperature below 5 °C and was completed after 20 minutes. The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours. Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL). The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated IN VACUO to give the crude product. The residue was purified by flash column chromatography (hexanes to 25percent ethyl acetate/hexanes) to afford the title compound (0. 51 g, 62percent) as a colorless oil. H NMR (CDCI3, 300 MHz) : 4. 70 (1H, m), 3. 96 (2H, m), 2. 24 (2H, m), 2. 08 (2H, M).
With pyridine; trifluoroacetic anhydride; In 1,4-dioxane; chloroform; ethyl acetate;
Preparation c-129 Tetrahydro-furan-2-carbonitrile Trifluoroacetic anhydride (1.55 g, 7.38 mmol) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0 C.) of tetrahydro-furan-2-carboxylic acid amide (0.77 g, 6.71 mmol) and pyridine (1.06 g, 13.42 mmol) in anhydrous 1,4-dioxane (10 mL). The addition of trifluoroacetic anhydride was monitored to keep the internal temperature below 5 C. and was completed after 20 minutes. The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours. Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL). The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated in vacuo to give the crude product. The residue was purified by flash column chromatography (hexanes to 25% ethyl acetate/hexanes) to afford the title compound (0.51 g, 62%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 4.70 (1H, m), 3.96 (2H, m), 2.24 (2H, m), 2.08 (2H, m).
62%
With pyridine; trifluoroacetic anhydride; In 1,4-dioxane; at 5 - 20℃; for 3.33333h;
Trifluoroacetic anhydride (1. 55 g, 7. 38 MMOL) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0 C) of tetrahydro-furan-2- carboxylic acid amide (0. 77 g, 6. 71 MMOL) and pyridine (1. 06 g, 13. 42 MMOL) in anhydrous 1, 4-dioxane (10 mL). The addition of TRIFLUOROACETIC anhydride was monitored to keep the internal temperature below 5 C and was completed after 20 minutes. The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours. Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL). The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated IN VACUO to give the crude product. The residue was purified by flash column chromatography (hexanes to 25% ethyl acetate/hexanes) to afford the title compound (0. 51 g, 62%) as a colorless oil. H NMR (CDCI3, 300 MHz) : 4. 70 (1H, m), 3. 96 (2H, m), 2. 24 (2H, m), 2. 08 (2H, M).
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