Imidazole → 2-(Tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanone

HRID 1807250Notes

Reaction equation

HRID 1807250 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20].O>CN(C=O)C>[Si:23]([O:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)=[O:4])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 3175522-Hydroxy-1-(4-nitrophenyl)ethanone

Product 1

HCID 199641862-(Tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanoneYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step A To a solution of 2-hydroxy-1-(4-nitrophenyl)ethanone (1 g, 5.52 mmol) in DMF (25 ml) was added imidazole (564 mg, 8.28 mmol), followed by the addition of tert-butylchlorodimethylsilane (915 mg, 6.07 mmol). The reaction mixture was stirred at room temperature for 3 h. The mixture was poured into H2O (25 mL) and extracted with ethyl acetate (3×25 mL). The organic layers were combined, washed with H2O (5×25 mL), brine (1×25 mL), dried over MgSO4 and concentrated in vacuo to give 2-(tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanone as a yellow solid (1.6 g, 98%).

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washwashed with H2O (5×25 mL), brine (1×25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-550c22b313934c2382cccdfb26142ec1
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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