1-(1-Methyl-1H-imidazol-2-yl)ethan-1-one → 2-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol

HRID 575053Notes

Reaction equation

HRID 575053 reaction equation
Br[Mg][C:3]#[CH:4].[CH3:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11](=[O:13])[CH3:12]>O1CCCC1>[CH3:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]([OH:13])([C:3]#[CH:4])[CH3:12]

Participants

4

Reactant 2

HCID 143396711-(1-Methyl-1H-imidazol-2-yl)ethan-1-oneHCID 178418486HCID 178418486, compound

Product 1

HCID 866930882-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-olYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed bromo(ethynyl)magnesium (0.5M in THF, 77 mL, 1.20 equiv). This was followed by the addition of a solution of 1-(1-methyl-1H-imidazol-2-yl)ethan-1-one (4.0 g, 32.22 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) dropwise with stirring at 0° C. in 20 min. The resulting solution was stirred for 20 min at 0° C. The resulting solution was allowed to react with stirring for an additional 5 h at room temperature. The reaction was then quenched by the addition of 50 mL of saturated aqueous NH4Cl. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/hexane (1/3) to give 2.8 g (58%) of 2-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol as a off-white solid. 1H-NMR (300 MHz, CDCl3, ppm) δ 7.065 (d, 1H), 6.842 (d, 1H), 3.935 (d, 3H), 3.092 (s, 3H), 1.950 (s, 3H).

Workup

  1. customInto a 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 20 min at 0° C
  4. customto react
  5. stirringwith stirring for an additional 5 h at room temperature
  6. customThe reaction was then quenched by the addition of 50 mL of saturated aqueous NH4Cl
  7. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7c11520656b24df38e12cb73cd5c033d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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