Tetrahydrofuran → 4-(1-Hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole

HRID 2213671Notes

Reaction equation

HRID 2213671 reaction equation
[CH3:1][C:2]([CH3:14])([O:4][C:5]([N:7]1[CH:11]=[C:10]([CH:12]=[O:13])[N:9]=[CH:8]1)=[O:6])[CH3:3].O1CCC[CH2:16]1>>[OH:13][CH:12]([C:10]1[N:9]=[CH:8][N:7]([C:5]([O:4][C:2]([CH3:14])([CH3:1])[CH3:3])=[O:6])[CH:11]=1)[CH3:16]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 15480636tert-Butyl 4-formyl-1H-imidazole-1-carboxylate

Product 1

HCID 219577164-(1-Hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole

Procedure

To a solution of 1-(dimethylethoxycarbonyl)imidazole-4-carboxaldehyde (9.3 g, 47 mmol) in tetrahydrofuran (200 mL) was added a methyl Grignard reagent (6.6 mL, 50 mmol) at ambient temperature. The resulting reaction mixture was stirred overnight at ambient temperature. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to afford 10 g of 4-(1-hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole as an oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1272e2970fe64025ad7a0ca46b3d227f
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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