반응 #75877

반응 방정식

2-methoxy-5-nitrophenol

imidazole

tert-butyldimethylsilyl chloride

→

product

수율 78.8%

1-(tert-Butyldimethylsilyl)oxy-2-methoxy-5-nitrobenzene

수율 78.8%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGto stir at room temperature for 16 h
3. 3
   기타The solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 40 mL of 50% ethyl acetate in hexanes
5. 5
   여과filtered through 10 g of silica gel
6. 6
   세척The silica gel was washed with an additional 200 mL of 50% ethyl acetate in hexanes
7. 7
   농축concentrated in vacuo

실험 절차

To a mixture of 2-methoxy-5-nitrophenol (1.53 g, 9.0 mmol) and imidazole (1.08 g, 15.9 mmol) in anhydrous DMF (40 mL) was added, with stirring, tert-butyldimethylsilyl chloride (2.05 g, 13.6 mmol) and the mixture was allowed to stir at room temperature for 16 h. The solvent was removed in vacuo and the residue was dissolved in 40 mL of 50% ethyl acetate in hexanes and filtered through 10 g of silica gel. The silica gel was washed with an additional 200 mL of 50% ethyl acetate in hexanes and the filtrates were combined and concentrated in vacuo to give 2.01 g of product as a tan crystalline solid. 1H NMR (CDCl3) δ 7.89 (dd, 1H, J=9.0 Hz, 2.8 Hz), 7.69 (d, 1H, J=2.8 Hz), 6.88 (d, 1H, J=9.0), 3.90 (s, 3H), 1.00 (s, 9H), 0.18 (s, 6H).

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