Imidazole → HCID 53924662, compound

HRID 396837Notes

Reaction equation

HRID 396837 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[OH:9])[CH3:2].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1.O>CN(C=O)C>[Si:13]([O:9][C:8]1[CH:7]=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[CH2:1][CH3:2])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 137241431-(3-Ethyl-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 53924662HCID 53924662, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(3-ethyl-4-hydroxyphenyl)-1-ethanone (9.24 g, 56.27 mmol) in DMF (60 ml) was added tert-butyldimethylsilyl chloride (9.33 g, 61.9 mmol), imidazole (4.6 g, 67.52 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was fractionally distilled under reduced pressure (180° C., 0.5 mmHg) to give title compound (12.3 g, 78% yield).

Workup

  1. extractionThe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was fractionally distilled under reduced pressure (180° C., 0.5 mmHg)

Sources & evidence

ORD record
ord-c1a9289e69414ef6afbade77b1e2be13
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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