반응 #1244261

반응 방정식

2-nitroimidazole

propargyl bromide

potassium carbonate

DMF

→

10

수율 85.5%

2-Nitro-1-(prop-2-ynyl)-1H-imidazole

수율 85.5%

용매

EtOAc

반응 조건

후처리

1. 1
   기타reaction
2. 2
   workup.ADDITIONThe reaction was poured onto water (20 mL)
3. 3
   추출extracted into EtOAc (3×20 mL)
4. 4
   세척The combined organics were washed with water (5×20 mL)
5. 5
   농축The organic layer was then concentrated in vacuo
6. 6
   기타purified on a silica gel cartridge

실험 절차

To a round bottom flask was added 2-nitroimidazole (500 mg, 4.42 mmol), propargyl bromide (631 mg, 5.31 mmol), potassium carbonate (733 mg, 5.31 mmol) and DMF (5 mL). The reaction was stirred overnight at RT. TLC (EtOAc) indicated complete reaction. The reaction was poured onto water (20 mL) and extracted into EtOAc (3×20 mL). The combined organics were washed with water (5×20 mL). The organic layer was then concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 571 mg (85% yield) of 10 as a pale yellow solid. 1H NMR (CDCl3, 400 MHz), δ: 2.63 (1H, d, J=5.6 Hz), 5.23 (2H, d, J=2.4 Hz), 7.20 (1H, d, J=1.2 Hz), 7.46 (1H, s). Mass Spec (lo-res): Calc'd for C6H5N3O2: 151.04; found: 152.10 (M+H).

출처