Dimethylformamide → 1-Pent-4-ynyl-1H-[1,2,3]triazole

Temperature

0 °C

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.

1. customTo a 50 mL round-bottomed flask equipped with a magnetic stirbar
2. temperatureto warm to ambient temperature
3. temperatureThe reaction mixture was then heated to 80° C.
4. stirringto stir for 2.5 hours
5. extractionextracted with ethyl acetate (2×20 mL)
6. dry with materialThe organic phase was dried with sodium sulfate
7. concentrationconcentrated de vacuo
8. customfollowed by a purification by column chromatography (ethyl acetate/hexane)

ORD record

ord-79c98c1ab3994ea69322c9936b99166e

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145395B2