反应 #6704

反应方程式

Isatin

sodium hydride

4-(3-bromophenyl)phenol benzyl ether

→

N-[3-(4-benzyloxyphenyl)phenyl]isatin

溶剂

DMF

反应条件

后处理

1. 1
   温度The reaction was heated in an oil-bath at 140° C
2. 2
   workup.WAITAfter ˜16 hours
3. 3
   温度the reaction was cooled to room temperature
4. 4
   浓缩concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (˜75 mL)
6. 6
   过滤filtered
7. 7
   浓缩The filtrate was concentrated under reduced pressure
8. 8
   其他to afford a sticky, brown solid which
9. 9
   其他was purified by preparative TLC on silica gel using 25% ethyl acetate in hexanes as the developing solvent

实验过程

Isatin (0.12 g, 0.81 mmol) in anhydrous DMF (30 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (21 mg, 1.1 equivalents). The reaction was stirred in ice for 0.5 hours and then warmed to room temperature. This solution was then treated with 4-(3-bromophenyl)phenol benzyl ether (Hajduk et al. J. Am. Chem. Soc. 1997, 119, 5818–5827), (0.16 g, 0.47 mmol) followed by copper iodide (0.32 g, 1.68 mmol). The reaction was heated in an oil-bath at 140° C. After ˜16 hours, the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (˜75 mL) and filtered. The filtrate was concentrated under reduced pressure to afford a sticky, brown solid which was purified by preparative TLC on silica gel using 25% ethyl acetate in hexanes as the developing solvent. Rf (product)=0.38. Yield=47 mg (25%); MALDI-TOF MS 407.02 obs. (405.5 calc.); 1H-NMR (CDCl3) 5.12 (s, 2H), 6.95 (d, 1H, J=8 Hz), 7.06 (d, 2H, J=8.8 Hz), 7.18 (t, 1H, J=7.5 Hz), 7.33–7.47 (m, 7H), 7.53 (d, 2H, J=8.8 Hz), 7.57–7.60 (m, 2H), 7.71 (d, 1H, J=7.5 Hz).

来源