Sodium ethoxide → HCID 67064546, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 268B (37.8 g, 0.101 mol) in ethanol (0.5 L) under nitrogen was reacted with sodium ethoxide in ethanol (21% by weight, 32.8 g, 0.104 mol) at room temperature. The mixture was slowly warmed to 50° C. and stirred for 1 hour at 40-50° C., cooled to 25° C., partitioned between ethyl acetate and water, and acidified to pH 4 with 1 M hydrochloric acid. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (12.0 g, 35%). 1H NMR (300 MHz, CDCl3) δ ppm 1.47 (t, J=7.17 Hz, 3 H) 4.52 (q, J=7.23 Hz, 2 H) 7.33 (d, J=5.15 Hz, 1 H) 7.50 (m, 3 H) 7.75 (d, J=5.52 Hz, 1 H) 7.88 (dd, J=7.72, 1.84 Hz, 2 H) 9.44 (s, 1 H) 14.16 (s, 1 H).

Provenance & Evidence