2-methyl-1-trityl-1H-imidazole-4-carbaldehyde → 2,2-dimethyl-1-(2-methyl-1-trityl-1H-imidazol-4-yl)propan-1-ol

HRID 216321Notes

Reaction equation

HRID 216321 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH3:6][C:7]1[N:8]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=[C:10]([CH:12]=[O:13])[N:11]=1>O1CCCC1>[CH3:2][C:1]([CH3:4])([CH3:3])[CH:12]([C:10]1[N:11]=[C:7]([CH3:6])[N:8]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:9]=1)[OH:13]

Participants

4

Reactant 2

HCID 150519362-methyl-1-trityl-1H-imidazole-4-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 686681432,2-dimethyl-1-(2-methyl-1-trityl-1H-imidazol-4-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyllithium (1.7 M in pentane) (1.7 mL, 2.8 mmol) was added slowly to an ambient temperature solution of 2-methyl-1-trityl-1H-imidazole-4-carboxaldehyde in tetrahydrofuran (10 mL) at 0° C. After stirring at ambient temperature for 2 h, the reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-60% ethyl acetate/hexane afforded 2,2-dimethyl-1-(2-methyl-1-trityl-1H-imidazol-4-yl)propan-1-ol.

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b42a10ac7864491a944adcd57435a86
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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