Reaction #7332

Reaction equation

t-butyldimethylsilyl chloride

4-nitrophenol

imidazole

t-butyldimethylsilyl chloride

→

1-nitro-4-(1,1,2,2-tetramethyl-1-silapropoxy)benzene

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for another 1 day
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (200 mL)
4. 4
   Washwashed with a mixture of water (100 mL) and aqueous 1N HCl (80 mL)
5. 5
   WashThe organic layer was then washed with water, saturated aqueous sodium bicarbonate solution and brine
6. 6
   Dryingdried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   OtherThe residue was purified by flash chromatography
10. 10
    Washeluting with ethyl acetate/hexanes (1:9, V/V)

Procedure

To a solution of 4-nitrophenol (5.0 g, 35.9 mmol) (Aldrich) in dimethylformamide (50 mL) was added imidazole (3.18 g, 46.7 mmol) (Aldrich) and t-butyldimethylsilyl chloride (6.49 g, 43.1 mmol) (Avocado Research Chemicals Ltd.). The reaction mixture was stirred at room temperature for 1 day. TLC analysis showed starting material was still present. Another portion of t-butyldimethylsilyl chloride (1.0 g, 6.63 mmol) was added and the mixture was stirred at room temperature for another 1 day. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with a mixture of water (100 mL) and aqueous 1N HCl (80 mL). The organic layer was then washed with water, saturated aqueous sodium bicarbonate solution and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate/hexanes (1:9, V/V) to afford 1-nitro-4-(1,1,2,2-tetramethyl-1-silapropoxy)benzene. (Yield 7.8 g, 86%).

Source