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

HRID 1095304Notes

Reaction equation

HRID 1095304 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-dimethylformamide at 20° C. The mixture is stirred at 20° C. for 1.5 hours. 50.0 mmol of ethyl bromoacetate [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 60 F). Rf=020 (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-62186a6ff02f4e0b944be47e4c49ca21
Source dataset
uspto-grants-2012_03
Patent number
US08138176B2

Reaction notes

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