5-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dione → 5-(3,5-Dimethylisoxazol-4-yl)-3-hydroxy-3-phenylindolin-2-one

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Reaction Conditions

Reaction Steps

5-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dione (24.2 g, 0.1 mol) was dissolved in anhydrous THF (400 mL) and cooled to 0° C. followed by dropwise addition of a 2.0 M solution of PhMgBr in THF (110 mL, 220.0 mmol). The ice-bath was removed, and the reaction was stirred under N2 for 30 min at which point TLC analysis indicated complete consumption of the starting material. The reaction mixture was quenched with saturated aqueous NH4Cl (100 mL), and extracted with EtOAc (3×100 ml). The combined organic layers were washed with saturated aqueous NaHCO3 (100 ml), brine (100 ml), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was evacuated under high vacuum to give the crude alcohol (30 g, 94%). 1H NMR (400 MHz, DMSO-d6): δ 10.50 (s, 1H), 7.22-7.32 (m, 6H), 7.09 (d, J=1.2 Hz, 1H), 6.99 (d, J=8.0 Hz, 1H), 6.71 (brs, 1H), 2.32 (s, 3H), 2.15 (s, 3H) MS (ESI) m/e [M+1]+ 321.

Provenance & Evidence