Imidazole → HCID 59516987, compound

HRID 2079111Notes

Reaction equation

HRID 2079111 reaction equation
N1C=CN=C1.Cl[Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9].CN(C=O)C.[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:34]=[C:33]([OH:35])[CH:32]=[C:27]([C:28]([O:30][CH3:31])=[O:29])[CH:26]=1>C(OCC)(=O)C.O>[CH3:31][O:30][C:28](=[O:29])[C:27]1[CH:32]=[C:33]([O:35][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:34]=[C:25]([C:24]([O:23][CH3:22])=[O:36])[CH:26]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 139400Triisopropylsilyl chloride

Product 1

HCID 59516987HCID 59516987, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 5.1 g of imidazole and 12.9 ml of chlorotriisopropylsilane to a 100 ml DMF solution containing 10.5 g of 5-hydroxyisophthalic acid dimethyl ester, the mixture was stirred at room temperature for 15 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with ice-cooled 1N hydrochloric acid, water and saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (21.53 g) as a colorless oil.

Workup

  1. washThe organic layer was washed with ice-
  2. temperaturecooled 1N hydrochloric acid, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-149739e758f247b293296205952d70d6
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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