Imidazole → HCID 57709087, compound

HRID 546835Notes

Reaction equation

HRID 546835 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[CH3:14][O:15][C:16]([C:18]1[O:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH2:40][CH3:41])([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([CH3:39])[CH:33]=3)[CH2:30][CH3:31])=[CH:25][C:24]=2[CH3:42])=[CH:21][CH:22]=1)=[O:17].C(OCC)C>CN(C)C=O>[CH3:14][O:15][C:16]([C:18]1[O:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([C:32]3[CH:37]=[CH:36][C:35]([O:38][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:34]([CH3:39])[CH:33]=3)([CH2:30][CH3:31])[CH2:40][CH3:41])=[CH:25][C:24]=2[CH3:42])=[CH:21][CH:22]=1)=[O:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 574434845-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-furan-2-carboxylic Acid Methyl Ester

Product 1

HCID 57709087HCID 57709087, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylsilyl chloride (42.24 mg, 0.28 mmol) and imidazole (47.7 mg, 0.701 mmol) were added to a solution of 5-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-furan-2-carboxylic acid methyl ester (Example 19-(1); 55 mg, 0.14 mmol) in N,N-dimethylformamide (0.2 mL) at room temperature, and the mixture was stirred at room temperature for 0.2 hour. Diethyl ether was added to the reaction solution. The organic layer was washed with distilled water and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=95/5 to ethyl acetate only) to give the title compound (61 mg, 86%).

Workup

  1. washThe organic layer was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=95/5 to ethyl acetate only)

Sources & evidence

ORD record
ord-e492c49aa676429bbb7ca3092bae1217
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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