Imidazole → HCID 22144737, compound

HRID 1063863Notes

Reaction equation

HRID 1063863 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([Br:12])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C)C=O>[Si:18]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([Br:12])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22144918286836-24-6

Product 1

HCID 22144737HCID 22144737, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.40 gm (1.76 mMol) 5-(hydroxymethyl)-7-bromobenzofuran, 0.24 gm (30.5 mMol) imidazole, and 0.26 gm (1.76 mMol) tert-butyldimethylsilyl chloride in 2 ml dimethylformamide was stirred at room temperature over night. The reaction mixture was then partitioned between hexane and water. The organic phase was washed with well with water, dried over magnesium sulfate and concentrated under reduced pressure to provide 0.51 gm (85%) of the desired compound.

Workup

  1. customThe reaction mixture was then partitioned between hexane and water
  2. washThe organic phase was washed with well with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c77c48f5917b496a8c8de29e11a18601
Source dataset
uspto-grants-2005_11
Patent number
US06967201B1

Reaction notes

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