5-碘-1-戊炔

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5-iodo-pent-1-yne (1.0 g, 5.2 mmol) in tert-BuNH2 (2.0 g. 27 mmol) was heated to reflux for 4 h, evaporated, diluted with Et2O, filtered, and concentrated to afford the title compound. 1H NMR (CDCl3) δ 2.67 (t, 2H), 2.27 (td, 2H), 1.96 (t, 1H), 1.70 (quint., 2H), 1.11 (s, 9H). to reflux for 4 h evaporated diluted with Et2O filtered concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-iodo-pent-1-yne (2.40 g, 12.3 mmol) and morpholine (2.70 g, 30.9 mmol) was heated to 80° C. for 15 min. The mixture was diluted with Et2O and filtered. The solid residue was discarded, and the mother liquor was extracted with 3N HCl. The aqueous layer was made basic with NaOH, and back-extracted into EtOAc. Drying (Na2SO4), and concentration gave the title compound as a pale orange oil. 1H NMR (CDCl3) δ 3.67 (t, 4H), 2.39 (m, 6H), 2.21 (td, 2H), 1.93 (t, 1H), 1.67 (quint., 2H). filtered the mother liquor was extracted with 3N HCl back-extracted into EtOAc Drying (Na2SO4), and concentration

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the manner of Example 100 above, 5-iodo-1-pentyne is reacted with 5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione to give the title compound, mp 226° C., THEORY: C, 53.4, H, 4.48, N, 4.15. FOUND: C, 53.3, H, 4.58, N, 4.13.

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 50 mL round-bottomed flask equipped with a magnetic stirbar was added 1-H-1,2,3-triazole (0.192 g, 2.78 mmol) and DMF (10 mL) and then cooled to 0° C. while stirring. Then, sodium hydride (60% dispersion in mineral oil) (0.133 g, 3.33 mmol) is added to the reaction mixture and was slowly allowed to warm to ambient temperature. Then, 1-iodo-4 pentyne (0.647 g, 3.33 mmol) was added dropwise. The reaction mixture was then heated to 80° C. and allowed to stir for 2.5 hours. Water (20 mL) was then added to the reaction mixture and then extracted with ethyl acetate (2×20 mL). The organic phase was dried with sodium sulfate and concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane) to produce 1-Pent-4-ynyl-1H-[1,2,3]triazole (0.349 g, 93%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.67 (s, 1H), δ 7.59 (s, 1H), δ 4.53 (t, 2H), δ 2.20 (t, 2H), δ 2.17 (m, 2H), δ 2.04 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 133.9, 123.9, 82.2, 70.4, 48.7, 28.9, 15.7 ppm; HRMS (ESI) calcd for C7H10N3 (M+) 136.0869, found 136.0866. To a 50 mL round-bottomed flask equipped with a magnetic stirbar to warm to ambient temperature The reaction mixture was then heated to 80° C. to stir for 2.5 hours extracted with ethyl acetate (2×20 mL) The organic phase was dried with sodium sulfate concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 50 mL round-bottomed flask equipped with a magnetic stirbar was added 1-H-1,2,3-triazole (0.192 g, 2.78 mmol) and DMF (10 mL) and then cooled to 0° C. while stirring. Then, sodium hydride (60% dispersion in mineral oil) (0.133 g, 3.33 mmol) is added to the reaction mixture and was slowly allowed to warm to ambient temperature. Then, 1-iodo-4 pentyne (0.647 g, 3.33 mmol) was added dropwise. The reaction mixture was then heated to 80° C. and allowed to stir for 2.5 hours. Water (20 mL) was then added to the reaction mixture and then extracted with ethyl acetate (2×20 mL). The organic phase was dried with sodium sulfate and concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane) to produce 1-Pent-4-ynyl-1H-[1,2,3]triazole (0.349 g, 93%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.67 (s, 1H), δ 7.59 (s, 1H), δ 4.53 (t, 2H), δ 2.20 (t, 2H), δ 2.17 (m, 2H), δ 2.04 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 133.9, 123.9, 82.2, 70.4, 48.7, 28.9. 15.7 ppm; HRMS (ESI) calcd for C7H10N3 (M+) 136.0869. found 136.0866. To a 50 mL round-bottomed flask equipped with a magnetic stirbar to warm to ambient temperature The reaction mixture was then heated to 80° C. to stir for 2.5 hours extracted with ethyl acetate (2×20 mL) The organic phase was dried with sodium sulfate concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 50 mL round-bottomed flask equipped with a magnetic stirbar was added 1-H-1,2,3-triazole (0.192 g, 2.78 mmol) and DMF (10 mL) and then cooled to 0° C. while stirring. Then, sodium hydride (60% dispersion in mineral oil) (0.133 g, 3.33 mmol) is added to the reaction mixture and was slowly allowed to warm to ambient temperature. Then, 1-iodo-4 pentyne (0.647 g, 3.33 mmol) was added dropwise. The reaction mixture was then heated to 80° C. and allowed to stir for 2.5 hours. Water (20 mL) was then added to the reaction mixture and then extracted with ethyl acetate (2×20 mL) The organic phase was dried with sodium sulfate and concentrated. de vacuo followed by a purification by column chromatography (ethyl acetate/hexane) to produce 1-Pent-4-ynyl-1H-[1,2,3]triazole (0.349 g, 93%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.67 (s, 1H), δ 7.59 (s, 1H), δ 4.53 (t, 2H), δ 2.20 (t, 2H), δ 2.17 (m, 2H), δ 2.04 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 133.9, 123.9, 82.2, 70.4, 48.7, 28.9. 15.7 ppm; HRMS (ESI) calcd for C7H10N3 (M+) 136.0869. found 136.0866. To a 50 mL round-bottomed flask equipped with a magnetic stirbar to warm to ambient temperature The reaction mixture was then heated to 80° C. to stir for 2.5 hours extracted with ethyl acetate (2×20 mL) The organic phase was dried with sodium sulfate concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5-iodo-pent-1-yne (1.0 g, 5.2 mmol) in tert-BuNH2 (2.0 g. 27 mmol) was heated to reflux for 4 h, evaporated, diluted with Et2O, filtered, and concentrated to afford the title compound. 1H NMR (CDCl3) δ 2.67 (t, 2H), 2.27 (td, 2H), 1.96 (t, 1H), 1.70 (quint., 2H), 1.11 (s, 9H). to reflux for 4 h evaporated diluted with Et2O filtered concentrated

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-iodo-pent-1-yne (2.40 g, 12.3 mmol) and morpholine (2.70 g, 30.9 mmol) was heated to 80° C. for 15 min. The mixture was diluted with Et2O and filtered. The solid residue was discarded, and the mother liquor was extracted with 3N HCl. The aqueous layer was made basic with NaOH, and back-extracted into EtOAc. Drying (Na2SO4), and concentration gave the title compound as a pale orange oil. 1H NMR (CDCl3) δ 3.67 (t, 4H), 2.39 (m, 6H), 2.21 (td, 2H), 1.93 (t, 1H), 1.67 (quint., 2H). filtered the mother liquor was extracted with 3N HCl back-extracted into EtOAc Drying (Na2SO4), and concentration

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 5-iodo-pent-1-yne (2.40 g, 12.3 mmol) and morpholine (2.70 g, 30.9 mmol) was heated to 80° C. for 15 min. The mixture was diluted with Et2O and filtered. The solid residue was discarded, and the mother liquor was extracted with 3N HCl. The aqueous layer was made basic with NaOH, and back-extracted into EtOAc. Drying (Na2SO4), and concentration gave the title compound as a pale orange oil. 1H NMR (CDCl3) δ 3.67 (t, 4H), 2.39 (m, 6H), 2.21 (td, 2H), 1.93 (t, 1H), 1.67 (quint., 2H). filtered the mother liquor was extracted with 3N HCl back-extracted into EtOAc Drying (Na2SO4), and concentration

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the manner of Example 100 above, 5-iodo-1-pentyne is reacted with 5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione to give the title compound, mp 226° C., THEORY: C, 53.4, H, 4.48, N, 4.15. FOUND: C, 53.3, H, 4.58, N, 4.13.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the manner of Example 100 above, 5-iodo-1-pentyne is reacted with 5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione to give the title compound, mp 226° C., THEORY: C, 53.4, H, 4.48, N, 4.15. FOUND: C, 53.3, H, 4.58, N, 4.13.

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 50 mL round-bottomed flask equipped with a magnetic stirbar was added 1-H-1,2,3-triazole (0.192 g, 2.78 mmol) and DMF (10 mL) and then cooled to 0° C. while stirring. Then, sodium hydride (60% dispersion in mineral oil) (0.133 g, 3.33 mmol) is added to the reaction mixture and was slowly allowed to warm to ambient temperature. Then, 1-iodo-4 pentyne (0.647 g, 3.33 mmol) was added dropwise. The reaction mixture was then heated to 80° C. and allowed to stir for 2.5 hours. Water (20 mL) was then added to the reaction mixture and then extracted with ethyl acetate (2×20 mL). The organic phase was dried with sodium sulfate and concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane) to produce 1-Pent-4-ynyl-1H-[1,2,3]triazole (0.349 g, 93%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.67 (s, 1H), δ 7.59 (s, 1H), δ 4.53 (t, 2H), δ 2.20 (t, 2H), δ 2.17 (m, 2H), δ 2.04 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 133.9, 123.9, 82.2, 70.4, 48.7, 28.9, 15.7 ppm; HRMS (ESI) calcd for C7H10N3 (M+) 136.0869, found 136.0866. To a 50 mL round-bottomed flask equipped with a magnetic stirbar to warm to ambient temperature The reaction mixture was then heated to 80° C. to stir for 2.5 hours extracted with ethyl acetate (2×20 mL) The organic phase was dried with sodium sulfate concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane)