Water → 5-(1-Hydroxyethyl)-1-methylimidazole

HRID 1064324Notes

Reaction equation

HRID 1064324 reaction equation
[CH3:1][Mg]Br.[CH:4]([C:6]1[N:10]([CH3:11])[CH:9]=[N:8][CH:7]=1)=[O:5].O>C(OCC)C.C1COCC1>[OH:5][CH:4]([C:6]1[N:10]([CH3:11])[CH:9]=[N:8][CH:7]=1)[CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 222735265-(1-Hydroxyethyl)-1-methylimidazoleYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Methyl magnesium bromide (100 ml of a 3M solution in diethyl ether, 0.30 mol) was added dropwise to a solution of 5-formyl-1-methylimidazole (14.5 g, 0.13 mol) in THF (750 ml) cooled to −20° C. such that the reaction temperature was kept below 3° C. The mixture was allowed to warm to ambient temperature and water (150 ml) was carefully added. The aqueous mixture was continuously extracted with EtOAc. The EtOAc extract was dried, and the volatiles removed by evaporation to give the title compound 14.4 g, (88%) as a solid product. NMR: 1.41 (d, 3H), 4.65-4.77 (m, 1H), 4.96-5.11 (m, 1H), 6.72 (s, 1H), 7.47 (s, 1H).

Workup

  1. customwas kept below 3° C
  2. temperatureto warm to ambient temperature
  3. extractionThe aqueous mixture was continuously extracted with EtOAc
  4. extractionThe EtOAc extract
  5. customwas dried
  6. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-4596dc158ea347dda83d8edf2f4fd374
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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