Potassium Sodium Tartrate → 5-(3-Hydroxypropyl)-1-methyl-2-ethylimidazole

Temperature

0 °C

To a cooled (0° C.) solution of ethyl 3-(1-methyl-2-ethylimidazol-5-yl)propionate (1.75 g, 8.33 mmol) in 30 ml of THF was added 4.6 ml (4.6 mmol) of 1M LAH solution in THF at 0° C. After stirring at 0° C. for 15 min, the mixture was allowed to warm and stirred at 20° C. for 0.7 h. Rochelle salt solution (equiv) was added and the mixture was stirred for 20 min. The aqueous mixture was extracted with methylene chloride and filtered. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica (10 cm column, methylene chloride/methanol, 6/1-6/1) followed by recrystallization from acetonitrile/ether and methylene chloride/hexane to afford 1.268 g (90%) of 5-(3-hydroxypropyl)-1-methyl-2-ethylimidazole, as a white solid, m.p. 69°-71° C.

1. temperatureto warm
2. stirringstirred at 20° C. for 0.7 h
3. stirringthe mixture was stirred for 20 min
4. extractionThe aqueous mixture was extracted with methylene chloride
5. filtrationfiltered
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by chromatography on silica (10 cm column, methylene chloride/methanol, 6/1-6/1)
9. customfollowed by recrystallization from acetonitrile/ether and methylene chloride/hexane

ORD record

ord-4b05a1c39d7a4c9d971a0d7f4e9c94b6

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05552420