Imidazole → HCID 59517188, compound

HRID 1161378Notes

Reaction equation

HRID 1161378 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH:10]=[O:11].N1C=CN=C1.Cl[Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25]>C(OCC)(=O)C.O>[CH3:16][O:15][C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([O:6][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:14]=1)[CH:10]=[O:11]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 139400Triisopropylsilyl chlorideHCID 53145613-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 59517188HCID 59517188, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 50 ml DMF solution containing 2.8 g of 3-hydroxy-5-methoxybenzaldehyde [CAS No. 57179-35-8] there were added 2.5 g of imidazole and 5.9 ml of chlorotriisopropylsilane. The mixture was stirred at room temperature for 14 hours and 30 minutes. 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 then 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 (5.7 g) as a light yellow 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-b4573b8c7dd749a68fa53c68ce29a8a5
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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