Imidazole → 1-(Ethoxymethyl)-1H-imidazole

Temperature

-70 °C

Imidazole (20 g) was dissolved in tetrahydrofuran (700 ml) under a nitrogen atmosphere, cooled to −70° C. and n-butyllithium (117.5 ml of a 2.5M solution in hexane) added dropwise, over 15 minutes. The mixture was allowed to warm to −20° C. and stirred at −20° C. for 30 minutes before the dropwise addition of chloromethyl ethyl ether (30.5 g). The mixture was allowed to warm to room temperature and stirred for a further hour. The solvent was removed under reduced pressure to give a residue which was triturated with dichloromethane and filtered through a short pad of Arbacel (trade mark) filter aid. The solvent was removed from the filtrate under reduced pressure to give a mobile oil which was distilled under reduced pressure (0.7 millibars, 0.53 mmHg) to give 1-ethoxymethylimidazole (20.8 g) as an oil.

1. temperatureto warm to −20° C.
2. temperatureto warm to room temperature
3. customThe solvent was removed under reduced pressure
4. customto give a residue which
5. customwas triturated with dichloromethane
6. filtrationfiltered through a short pad of Arbacel (trade mark)
7. filtrationfilter aid
8. customThe solvent was removed from the filtrate under reduced pressure
9. customto give a mobile oil which
10. distillationwas distilled under reduced pressure (0.7 millibars, 0.53 mmHg)

ORD record

ord-4da54e537ed0492d9d8deb73e2a317e0

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06207678B1