1-Methylimidazole → HCID 22716723, compound

HRID 1583120Notes

Reaction equation

HRID 1583120 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.C([Li])CCC.[CH3:12][S:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1>C1COCC1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:18]([C:17]1[CH:20]=[CH:21][C:14]([S:13][CH3:12])=[CH:15][CH:16]=1)[OH:19]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 769854-(Methylthio)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 22716723HCID 22716723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-methylimidazole (10.0 g, 122 mmol) in 500 mL THF at −78° C. was added n-butyllithium (2.5 M in hexanes, 48.7 mL, 118 mmol) dropwise and the resulting solution was stirred at −78° C. for 30 min. 4-(Methylthio)benzaldehyde (14.73 mL, 110 mmol) was then added at −78° C. and the mixture was stirred until completion by TLC, and quenched with NH4Cl (sat). The mixture was then diluted with EtOAc, extracted and washed (NaHCO3 (sat.), brine). The organic phase was dried over MgSO4, filtered and concentrated. Crystallization (EtOAc/Hexanes) yielded (1-Methyl-1H-imidazol-2-yl)[4-(methylthio)phenyl]methanol.

Workup

  1. stirringthe mixture was stirred until completion by TLC
  2. customquenched with NH4Cl (sat)
  3. additionThe mixture was then diluted with EtOAc
  4. extractionextracted
  5. washwashed (NaHCO3 (sat.), brine)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCrystallization (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-cb1f3a89c38743819790be8dcea4eb6e
Source dataset
uspto-grants-2004_05
Patent number
US06740666B2

Reaction notes

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