Sodium bis(trimethylsilyl)amide → HCID 22472035, compound

Participants

Reaction Steps

Sodium bis(trimethylsilyl) amide (0.6 N, 7.09 mL, 4.25 mmol) was added dropwise into a cold (0° C.) mixture of 5-methoxy-2-(4-methoxyphenyl)-1H-inden-1,3(2H)-dione (1000 mg, 3.54 mmol) and tetrahydrofuran (15 mL). The mixture was allowed to stir for 1.0 h. Phenyl lithium (4.13 mL, 7.44 mmol) was added dropwise into the mixture at 0° C. The reaction mixture was allowed to warm to RT and stirred for 2 h. The reaction was quenched with 2 N HCl, poured into water, and extracted with ethyl acetate. The organic extracts were washed with brine and dried over MgSO4. Evaporation and flash chromatography (30%-50% ethyl acetate/petroleum ether) gave 3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-3-phenyl-indan-1-one as a light red foam and 3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-3-phenyl-indan-1-one as a light orange solid: mp 68-70; MS m/e 361 (M+H)+.

Provenance & Evidence