Triethylamine → (3-Azido-2-methylpropenyl)-benzene

Temperature

0 °C

To a 100 mL round-bottomed flask equipped with a magnetic stir was added trans-2-methyl-3-phenyl-2-propen-1-ol (2.00 g, 13.5 mmol) and 75 mL of methylene chloride. The solution was then cooled to 0° C. while stirring. Then, triethylamine (2.75 g, 27.0 mmol) is added followed by a dropwise addition of methanesulfonyl chloride (2.34 g, 20.4 mmol) and a two hour stir period. The reaction mixture is washed with water (2×75 mL), dried with sodium sulfate and then concentrated de vacuo. The crude mixture is then dissolved in 75 mL of DMF and then stirred via magnetic stir bar. To this mixture, sodium azide (1.76 g, 27.0 mmol) is added. The reaction mixture is then heated to 80° C. and allowed to stir for two hours. At this time, volatiles are concentrated de vacuo and the resulting residue is purified via column chromatography (1:9 ethyl acetate/hexane) providing (3-Azido-2-methyl propenyl)-benzene (2.08 g, 89%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.36-7.25 (m, 5H), δ 6.53 (s, 1H), δ 3.87 (s, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 129.4, 129.2, 128.9, 128.6, 128.4, 127.1, 59.9, 52.0, 22.3, 16.5 ppm; LRMS (EI) calcd for C10H11N3(M+) 173, found 173.

1. customTo a 100 mL round-bottomed flask equipped with
2. stirringwhile stirring
3. stirringstir period
4. washThe reaction mixture is washed with water (2×75 mL)
5. dry with materialdried with sodium sulfate
6. concentrationconcentrated de vacuo
7. dissolutionThe crude mixture is then dissolved in 75 mL of DMF
8. stirringstirred via magnetic stir bar
9. temperatureThe reaction mixture is then heated to 80° C.
10. stirringto stir for two hours
11. concentrationAt this time, volatiles are concentrated de vacuo
12. customthe resulting residue is purified via column chromatography (1:9 ethyl acetate/hexane)

ORD record

ord-6325b790c95545c7b17561fe5959b7c0

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367713B2