Imidazole → 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethan-1-one

HRID 2391088Notes

Reaction equation

HRID 2391088 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[C:19]([Si:16]([CH3:18])([CH3:17])[O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 84873-HydroxyacetophenoneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 143614891-(3-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3′-hydroxyacetophenone (0.500 g, 3.67 mmol) and imidazole (0.500 g, 7.34 mmol) in CH2Cl2 (5 mL) was added tert-butyldimethylsilyl chloride (0.609 g, 4.04 mmol), and the reaction was stirred for 1 hour at room temperature. The mixture was partitioned between CH2Cl2 and H2O, and the aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and H2O
  2. customthe aqueous layer was separated
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9a2bb1a2baf404c8876622ef6684ca8
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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