반응 #510018

반응 방정식

1-(diphenylmethyl)-1H-indole-2,3-dione

3-(benzyloxy)phenol

iso-propylmagnesium chloride

→

3-[4-(benzyloxy)-2-hydroxyphenyl]-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

수율 97.0%

용매

dichloromethane

tetrahydrofuran

반응 조건

후처리

1. 1
   농축concentrated in vacuo to dryness
2. 2
   workup.ADDITIONDichloromethane (100 mL) was added
3. 3
   workup.STIRRINGThe mixture was stirred at ambient temperature for 16 h
4. 4
   기타quenched with saturated ammonium chloride solution
5. 5
   세척The organic layer was washed with water
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   농축The filtrate was concentrated in vacuo to dryness
9. 9
   기타The obtained solid was recrystallized from ethyl acetate/hexanes

실험 절차

To a stirred solution of 3-(benzyloxy)phenol (8.7 g, 43.5 mmol) in tetrahydrofuran (100 mL) was added iso-propylmagnesium chloride (22.7 mL, 2 M tetrahydrofuran solution, 45.4 mmol) slowly at 0° C. The mixture was allowed to stir at 0° C. for 30 min, and concentrated in vacuo to dryness. Dichloromethane (100 mL) was added, followed by the addition of a solution of 1-(diphenylmethyl)-1H-indole-2,3-dione (12.4 g, 39.5 mmol) in dichloromethane (50 mL) at 0° C. The mixture was stirred at ambient temperature for 16 h, and quenched with saturated ammonium chloride solution. The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The obtained solid was recrystallized from ethyl acetate/hexanes to afford 3-[4-(benzyloxy)-2-hydroxyphenyl]-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (19.60 g, 97%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.49-7.43 (m, 1H), 7.42-7.25 (m, 13H), 7.23-7.17 (m, 2H), 7.12-7.04 (m, 2H), 6.91 (s, 1H), 6.72-6.62 (m, 2H), 6.51-6.44 (m, 1H), 6.39 (dd, J=8.6, 2.4 Hz, 1H), 4.99 (s, 2H); MS (ES+) m/z 536.3 (M+23).

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