Water → 2-(1-Phenylimidazol-2-yl)ethanol

HRID 566259

Reaction equation

HRID 566259 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:17]1[O:19][CH2:18]1.O>O1CCCC1.CCCCCC>[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[CH2:17][CH2:18][OH:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 815951-PhenylimidazoleHCID 178418339Butyllithium

Product 1

HCID 212657882-(1-Phenylimidazol-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

1-Phenylimidazole (3.00 g) was dissolved in tetrahydrofuran. To the solution was added dropwise a solution of n-butyllithium (1.6 M) in hexane (16.9 ml) at −70° C. The mixture was stirred for 30 minutes at the same temperature, to which 50% solution (4.76 g) of ethyleneoxide in tetrahydrofuran. The mixture was warmed up to room temperature over 1 hour, and stirred 19 hours at the same temperature. To the reaction mixture was added water. The mixture was subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to column chromatography on silica gel (developing solvent: ethyl acetate-methanol 100:0→93:7) to give the title compound.

Workup

  1. extractionThe mixture was subjected to extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-d006f90833324f769be06f53a13192b2
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Linked notes

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