Reaction #696697

Reaction equation

4-bromo-2-methyl-2-butene

sodium

2-nitroimidazole

→

1-(3-methyl-2-butenyl)-2-nitroimidazole

Yield 80.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherthe solvent was removed
2. 2
   Otherto leave a crude semi-solid which
3. 3
   Otherwas purified by column chromatography on silica

Procedure

To the sodium salt of 2-nitroimidazole prepared above was added acetonitrile (50 ml), 15-crown-5-ether (3.5 ml, 14.3 mmol) and 4-bromo-2-methyl-2-butene (2 ml; 17.4 mmol). The mixture was stirred at RT for ca 16 h. and then the solvent was removed to leave a crude semi-solid which was purified by column chromatography on silica. The intermediate product, 1-(3-methyl-2-butenyl)-2-nitroimidazole (80% yield) was eluted using a mixture of petroleum ether (40-60)/ethyl acetate (ratio 4:1 respectively).

Source