Phosphorus oxychloride → HCID 53677500, compound

Participants

Reaction Conditions

Reaction Steps

Phosphorous oxychoride (0.65 g, 4.16 mmol) was added dropwise to DMF (3 mL) at 0° C. After 0.5 hour, Example 7b (0.81 g, 3.70 mmol) in DMF (3 mL) was added at 0° C., then the mixture warmed to 35° C. for 0.75 hour. The solution was cooled to ambient temperature and crushed ice (10 g) was added. Solid sodium bicarbonate was added and to pH 8, the mixture diluted with water (100 mL), and the aqueous extracted with ethyl acetate (3×). The organic phase was separated, dried over anhydrous sodium sulfate, and the solvent removed in vacuo. The residue was chromatographed (eluting ethyl acetate/hexanes) to yield 0.39 g of the title compound as a purple solid; MS(CI/NH3) m/e 244 (M+H)+. 1H NMR(CDCl3, 300 MHz) δ3.68 (s, 3H), 4.26 (m, 2H), 5.14 (m, 1H), 7.06 (d, 1H), 7.18 (m, 3H), 7.84 (d, 1H), 9.09 (br s, 1H), 9.88 (s, 1H).

Provenance & Evidence