4-(1-Hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole → tert-butyl 4-acetyl-1H-imidazole-1-carboxylate

HRID 2213672Notes

Reaction equation

HRID 2213672 reaction equation
[OH:1][CH:2]([C:4]1[N:5]=[CH:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1)[CH3:3]>C(Cl)Cl.O=[Mn]=O>[C:2]([C:4]1[N:5]=[CH:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 21957605tert-butyl 4-acetyl-1H-imidazole-1-carboxylateYield 46.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(1-Hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole (8.7 g, 41 mmol) was dissolved in methylene chloride (100 mL) and MnO2 (10.7 g, 123 mmol) was added. The resulting reaction mixture was stirred overnight at ambient temperature. The reaction mixture was filtered, concentrated, and purified with silica column chromatography to afford 4 g of 4-acetyl-1-(dimethylethoxycarbonyl)imidazole and unreacted starting material.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified with silica column chromatography

Sources & evidence

ORD record
ord-fee662d6d17347dd8b9e68680efda31c
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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