alpha-Ethyl-1-(triphenylmethyl)-1H-imidazole-4-methanol → HCID 22285048, compound

HRID 2043620Notes

Reaction equation

HRID 2043620 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]([OH:28])[CH2:26][CH3:27])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.O=[Mn]=O>[C:1]([N:20]1[CH:24]=[C:23]([C:25](=[O:28])[CH2:26][CH3:27])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 12344795alpha-Ethyl-1-(triphenylmethyl)-1H-imidazole-4-methanol

Product 1

HCID 22285048HCID 22285048, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

In a 50 ml three-necked flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, 1-(1-trityl-1H-imidazol-4-yl)propan-1-ol x88 (1.21 g, 3.3 mmol) and MnO2 (2.85 g, 33 mmol) are dissolved in 20 ml of dioxane and the mixture is brought to reflux for 1 h. The mixture is filtered on Celite and the solvent is evaporated. Purification by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 90/9/1 (v/v/v)) affords 0.96 g of pure 1-(1-trityl-1H-imidazol-4-yl)propan-1-one x89.

Workup

  1. temperatureto reflux for 1 h
  2. filtrationThe mixture is filtered on Celite
  3. customthe solvent is evaporated
  4. customPurification by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 90/9/1 (v/v/v))

Sources & evidence

ORD record
ord-5543972aaa6e4152b27dd5d9954af1e0
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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