Jones' reagent → 2'-Oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1',2'-dihydro-3H-spiro[furo[2,3-b]pyridine-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylic acid

Participants

Reaction Steps

Freshly prepared Jones reagent was added drop wise to a solution of 5-(hydroxymethyl)-1′-((2-(trimethylsilyl)ethoxy)methyl)-3H-spiro[furo[2,3-b]pyridine-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (0.24 g, 0.60 mmol) in acetone (10 mL) at 0° C. until the starting material was completely consumed. The acidic mixture was neutralized carefully with saturated aqueous sodium bicarbonate solution and acidified with saturated aqueous citric acid solution to pH 5-6, then extracted with ethyl acetate (5×). The combined organic layers were dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane to give the title compound as a racemic mixture. MS: m/z=414.2 (M+1); 1H NMR (300 MHz, CD3OD): δ 8.70 (d, 1H, J=1.8 Hz), 8.34 (dd, 1H, J=1.5, 5.3 Hz), 8.29 (d, 1H, J=1.8 Hz), 7.89 (dd, 1H, J=1.5, 7.4 Hz), 7.19 (dd, 1H, J=5.3, 7.4 Hz), 5.26 (s, 2H), 3.78-3.65 (m, 4H), 0.95 (t, 2H, J=8 Hz), 0.005 (s, 9H).

Provenance & Evidence