反応 #7332

反応方程式

t-butyldimethylsilyl chloride

4-nitrophenol

imidazole

t-butyldimethylsilyl chloride

→

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

溶媒

dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for another 1 day
2. 2
   濃縮The reaction mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (200 mL)
4. 4
   洗浄washed with a mixture of water (100 mL) and aqueous 1N HCl (80 mL)
5. 5
   洗浄The organic layer was then washed with water, saturated aqueous sodium bicarbonate solution and brine
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他The residue was purified by flash chromatography
10. 10
    洗浄eluting with ethyl acetate/hexanes (1:9, V/V)

実験手順

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%).

出典