Imidazole → HCID 10497685, compound

HRID 2378534Notes

Reaction equation

HRID 2378534 reaction equation
[Br:1][C:2]1(OC)[C:9]([OH:10])=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH2:3]1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].O.CN([CH:30]=[O:31])C>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:31][CH3:30])[C:9]=1[O:10][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:5]=[O:6]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6228Dimethylformamide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 178486329HCID 178486329, compound

Product 1

HCID 10497685HCID 10497685, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of 3-bromovanillin (1.16 g, TCI) in anhydrous DMF (20 ml) was added with imidazole (408 mg, TCI), added dropwise with a solution of 4-(N,N-dimethylamino)pyridine (25 mg) and t-butyldimethylsilyl chloride (904 mg, TCI) in DMF (15 ml) under ice cooling, stirred 30 minutes, then warmed to room temperature, and further stirred 3 hours. The reaction mixture was added with water (100 ml), and extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (Intermediate 16, 1.75 g).

Workup

  1. customfurther stirred 3 hours
  2. extractionextracted with ethyl acetate (100 ml)
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-1ad4653be1aa4e0f9259412c8c14235b
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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