4-Toluenesulfonyl chloride → 3-(2-Azidoethyl)thiophene

Temperature

0 °C

2-(3-Thienyl)ethyl alcohol (2.62 g, 20.4 mmol) was dissolved in DCM (100 mL) and cooled to 0° C. After addition of triethylamine (3.10 g, 30.6 mmol) and solid tosyl chloride (3.89 g, 20.4 mmol), the reaction was stirred at room temperature overnight. DCM was evaporated, the mixture was diluted with EtOAc and washed subsequently with aqueous hydrochloric acid (1 N), water, saturated sodium hydrogen carbonate and brine. Drying and evaporation afforded an oil, which was dissolved in anhydrous DMF (20 mL). Sodium azide (2.65 g, 40.8 mmol) was added and the mixture heated to 40° C. for 3 h. After cooling to room temperature, EtOAc was added and the solution was washed with water (4×) and brine, then dried and evaporated. The resulting oil was filtered over silica gel (100 g) with the aid of PE/EtbAc (10:1) to obtain 2-(3-thienyl)ethyl azide (2.45 g, 78% ) as a colorless liquid. 1H-NMR (CDCl3) δ 7.3 (dd, J=2.9, 4.9 Hz, 1 H), 7.07 (m, 1 H), 6.98 (dd, J=1.2, 4.9 Hz, 1 H), 3.51 (t, J=7.1 Hz, 2 H), 2.94 (t, J=7.1 Hz, 2 H).

1. customDCM was evaporated
2. additionthe mixture was diluted with EtOAc
3. washwashed subsequently with aqueous hydrochloric acid (1 N), water, saturated sodium hydrogen carbonate and brine
4. customDrying
5. customevaporation
6. customafforded an oil, which
7. temperaturethe mixture heated to 40° C. for 3 h
8. temperatureAfter cooling to room temperature
9. washthe solution was washed with water (4×) and brine
10. customdried
11. customevaporated
12. filtrationThe resulting oil was filtered over silica gel (100 g) with the aid of PE/EtbAc (10:1)

ORD record

ord-4eb505c89bdc4e3aa9a3c47514b38a64

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119073B2