반응 #43544

반응 방정식

5-fluoroisatin

sodium hydride

p-methoxybenzyl chloride

→

5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione

수율 82.4%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONafter the addition of the last portion
2. 2
   workup.STIRRINGto stir for 1 hour
3. 3
   기타The reaction was then quenched by slow addition of excess methanol
4. 4
   기타After bubbling
5. 5
   workup.ADDITIONthe reaction was poured into water (100 mL)
6. 6
   추출extracted twice with ethyl acetate
7. 7
   건조dried over MgSO4
8. 8
   기타the solvent was removed
9. 9
   기타The residue was purified by silica gel chromatography

실험 절차

A solution of 5-fluoroisatin (5 g, 30.2 mmol) in DMF (60 mL) was cooled in an ice/water bath and treated with sodium hydride (1.44 g, 60.6 mmol) portionwise. The reaction was stirred for 15 minutes after the addition of the last portion and then treated with p-methoxybenzyl chloride (5.32 g, 45.3 mmol) and allowed to stir for 1 hour. The reaction was then quenched by slow addition of excess methanol. After bubbling had stopped, the reaction was poured into water (100 mL) and extracted twice with ethyl acetate. The organics were combined, dried over MgSO4 and the solvent was removed. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 7.1 g (82%) of 5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione; 1H NMR (CDCl3, 400 MHz) δ 3.79 (s, 3H), 4.86 (s, 2H), 6.75 (dd, 1H, J1=3.6, J2=8.6), 6.84-6.90 (m, 2H), 7.19 (ddd, 1H, J1=J2=8.6, J3=3.6), 7.22-7.27 (m, 1H), 7.26-7.31 (m, 2H); HPLC-MS calcd. for C16H12FNO3 (M+H+) 286.1, found 286.3.

출처