반응 #6704

반응 방정식

Isatin

sodium hydride

4-(3-bromophenyl)phenol benzyl ether

→

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

용매

DMF

반응 조건

후처리

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

실험 절차

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).

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