Reaktion #510018

Reaktionsgleichung

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

Ausbeute 97.0%

Lösungsmittel

dichloromethane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated 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
   Sonstigequenched with saturated ammonium chloride solution
5. 5
   WaschenThe organic layer was washed with water
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   EinengenThe filtrate was concentrated in vacuo to dryness
9. 9
   SonstigeThe obtained solid was recrystallized from ethyl acetate/hexanes

Vorschrift

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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