Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Methylimidazole | HCID 12749 | — |
| Reactant | 3-Bromo-1,2-propanediol | HCID 20827 | — |
| Reactant | HCID 178418922 | HCID 178418922 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 15597006 | HCID 15597006 | 81.2% |
Reaction Steps
A200 ml flask was charged with 2.0 g of t-butoxypotassium, 70 ml of tetrahydrofuran, 1.23 g of 2-methylimidazole. After stirring for 30 minutes, a solution of 2.5 g of 2,3-dihydroxyl-n-propyl bromide in 5 ml of t-butanol was added. After refluxing for one hour, 5 ml of 1 N HCl solution was added and the mixture was allowed to stand over night. The solvent was evaporated under reduced pressure. The residue was extracted with dichloromethane, washed with saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous magnesium sulfate. After removing anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (development solvent: methyl acetate/methanol=90/10) to obtain 1.9 g of 1-(2′,3′-dihydroxylpropyl)-2-methylimidazole (compound (A-1)). 1H-NMR spectrum of the resulting compound is shown in FIG. 1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07314701B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-2bed1feeb64e48b9a611cfa7273656a8 |
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| Source note | uspto-grants-2008_01 |
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