반응 #7332

반응 방정식

t-butyldimethylsilyl chloride

4-nitrophenol

imidazole

t-butyldimethylsilyl chloride

→

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

용매

dimethylformamide

반응 조건

후처리

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

실험 절차

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%).

출처