Hydrochloric Acid → 1H-imidazol-2-yl(2-iodophenyl)methanol

HRID 735342Notes

Reaction equation

HRID 735342 reaction equation
C([Li])CCC.CN(C[N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)C.[I:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].Cl>O1CCCC1>[NH:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH:18]([C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[I:15])[OH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6434392-IodobenzaldehydeHCID 38320731-(1H-Imidazol-1-yl)-N,N-dimethylmethanamineHCID 178418339Butyllithium

Product 1

HCID 689021281H-imidazol-2-yl(2-iodophenyl)methanolYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium solution (2.5M in hexanes, 0.84 mL, 2.10 mmol) was added to 1-(dimethylaminomethyl)imidazole (prepared by the method detailed in JOC 1988, 53, 5685-5689; 0.25 g, 2.0 mmol) in tetrahydrofuran (8 mL) at ≦−65° C. with stirring under nitrogen. After 1 hour at this temperature a solution of 2-iodobenzaldehyde (0.50 g, 2.09 mmol) in tetrahydrofuran (1 mL) was added and the mixture allowed to return to ambient temperature overnight. Dilute hydrochloric acid (2N, 10 mL) was then added and organic solvent removed in vacuo before neutralising with sodium bicarbonate. Dichloromethane (3×30 mL) extracts were washed with saturated brine then dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. Purification by flash column chromatography eluting with 50% ethyl acetate/isohexane gave a white solid of 1H-imidazol-2-yl(2-iodophenyl)methanol (0.22 g, 38%). 1H NMR (500 MHz, d6-DMSO) δ 11.94 (1H, s), 7.80 (1H, dd, J=1.0, 7.8 Hz), 7.53 (1H, dd, J=1.7, 7.8 Hz), 7.41-7.37 (1H, m), 7.04-7.00 (2H, m), 6.74 (1H, s), 6.20 (1H, d, J=4.7 Hz), 5.83 (1H, d, J=4.7 Hz); m/z (ES+) 301 [MH+].

Workup

  1. customprepared by the method
  2. customorganic solvent removed in vacuo
  3. washDichloromethane (3×30 mL) extracts were washed with saturated brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customPurification by flash column chromatography
  9. washeluting with 50% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-1e6f5bccc6334795b746d9173c396693
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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