Imidazole → alpha-Methyl-1H-imidazole-1-ethanol

Chloroacetone (9.25 g.) in dry acetonitrile was added dropwise with stirring and ice cooling to a slurry of imidazole (13.6 g.) in acetonitrile (100 ml.). The mixture was stirred for 4 hours with ice cooling and then for 24 hours at room temperature. The solvent was removed and the product isolated by chromatography on silica gel, eluting with 10% methanol/dichloromethane. This material in 100 ml. of methanol was treated with excess sodium borohydride at 0° C. for 1 hours and acidified with methanolic hydrogen chloride. The solvent was removed, ethyl acetate added and the stirred mixture treated dropwise with saturated potassium carbonate solution until basic. The ethyl acetate was then decanted, dried, evaporated and the residue chromatographed on silica gel eluting with 10% methanol/dichloromethane to give pure 1-(2-hydroxypropyl)imidazole.

1. stirringThe mixture was stirred for 4 hours with ice cooling
2. customThe solvent was removed
3. customthe product isolated by chromatography on silica gel
4. washeluting with 10% methanol/dichloromethane
5. additionof methanol was treated with excess sodium borohydride at 0° C. for 1 hours
6. customThe solvent was removed
7. additionethyl acetate added
8. additionthe stirred mixture treated dropwise with saturated potassium carbonate solution until basic
9. customThe ethyl acetate was then decanted
10. customdried
11. customevaporated
12. customthe residue chromatographed on silica gel eluting with 10% methanol/dichloromethane

ORD record

ord-4387f957540f457fb4224097e3c1689f

Source dataset

uspto-grants-1977_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04045568