Water → HCID 10512306, compound

HRID 1597453Notes

Reaction equation

HRID 1597453 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[CH:3]1.[Li]CCCC.[CH2:18]1[O:20][CH2:19]1.O>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]=[C:3]1[CH2:18][CH2:19][OH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6354Ethylene Oxide2×HCID 27487821-methyl-4-phenyl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 10512306HCID 10512306, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 674 mg (4.26 mmol) of 1-methyl-4-phenylimidazole (Kashima, C.; Harada, Y.; Hosomi, A. Heterocycles 1993, 35, 433) in 8.5 mL of THF at −78° C. was treated with 1.9 mL (4.69 mmol) of a 2.5 M nBuLi in hexanes solution. After stirring for 10 min, 1.1 mL (21.3 mmol) of ethylene oxide was added. The reaction was stirred for min then warmed to 25° C. and stirred for 1 h. Upon cooling to 0° C., 1.1 mL (21.3 mmol) of ethylene oxide was added, and the reaction was warmed to 25° C. and stirred overnight. The reaction was poured into H2O and extracted with Et2O. The combined organics were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography using EtOAc/MeOH (95:5), and the collected product was recrystallized from CH2Cl2/EtOAc to give 178 mg (21%) of title compound as a white solid: low resolution MS (ES) m/e 225 (MNa+), 203 (MH+).

Workup

  1. stirringThe reaction was stirred for min
  2. stirringstirred for 1 h
  3. temperatureUpon cooling to 0° C.
  4. temperaturethe reaction was warmed to 25° C.
  5. stirringstirred overnight
  6. extractionextracted with Et2O
  7. dry with materialThe combined organics were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel flash column chromatography
  11. customthe collected product was recrystallized from CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-b2541b840c0f4aa78d199d30112c5a35
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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