Potassium Iodide → ethyl (1-trityl-1H-imidazol-4-ylmethoxy)acetate

HRID 1360139Notes

Reaction equation

HRID 1360139 reaction equation
[H-].[Na+].[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][OH:28])[N:24]=[CH:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].[I-].[K+]>CN(C)C=O.O>[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][O:28][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:24]=[CH:23]1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetate2×HCID 24758Sodium hydride2×HCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 86632954ethyl (1-trityl-1H-imidazol-4-ylmethoxy)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

58.0 mmol of sodium hydride (60% dispersion in paraffin) are added in portions to a solution of 30.0 mmol of (1-trityl-1H-imidazol-4-yl)methanol [33769-07-2] in 300 ml of N,N-dimethyl-formamide at 20° C. The mixture is stirred at 20° C. for 1.5 hours. 50.0 mmol of ethyl bromo-acetate [105-36-2] and 6.00 mmol of potassium iodide are added, and the mixture is stirred at room temperature for 16 hours. A further 58.0 mmol of sodium hydride and 50 mmol of ethyl bromoacetate are added and the mixture is stirred again for 16 hours. The reaction mixture is poured into water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried with magnesium sulphate and evaporated. The title compound is obtained as a brown oil from the residue by flash chromatography (SiO2 60F). Rf=0.20 (ethyl acetate-heptane 2:1), Rt=4.32 (gradient I).

Workup

  1. stirringthe mixture is stirred at room temperature for 16 hours
  2. stirringthe mixture is stirred again for 16 hours
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-783f59a75d63487d955954a2a148e793
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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