Sodium hydride → HCID 71062618, compound

Participants

Reaction Steps

A solution of 1C (25 g, 95 mmol) in DMF (40 mL) was added over a period of 30 min to an ice cold solution of NaH (9.53 g, 238 mmol) in DMF (20 mL), and the mixture was stirred for 10 min. Trifluoroethyl iodide (50 g, 238 mmol) was then added, and the mixture was stirred for 3 h at room temperature. The reaction mixture was then brought to 0° C., excess NaH was quenched with ice water, and the aqueous layer with extracted with ethyl acetate (2×200 mL). The combined organic layers were dried over sodium sulfate and filtered, and the filtrate was concentrated under vacuum to give the title compound (16.2 g, 42%) as a solid. 1H NMR (300 MHz, CDCl3): δ 8.02 (d, J=9.3 Hz, 1H), 6.85 (dd, J1=2.7 Hz, J2=9.0 Hz, 1H), 6.68 (d, J=2.7 Hz, 1H), 4.1 (q, J=6.9 Hz, 2H), 3.86 (s, 3H), 3.05-2.9 (m, 4H), 2.6-2.4 (m, 4H), 1.23 (t, J=6.9 Hz, 3H). ESI-MS m/z: 345 (M+H)+.

Provenance & Evidence