Sodium hydride → HCID 73197847, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, Compound V (433 g, 1.37 mol) was dissolved in dry DMF (1.6 L) and to this sodium hydride (60% in oil, 60.4 g, 1.51 mol) was added. To the resulting orange solution, p-fluorobenzaldehyde (185 mL, 1.71 mol) was added and heated at 80° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (3 L) and extracted with water (3 ×1 L), then brine (1×1 L). The organic layer was dried over anhydrous sodium sulfate, filtered and solvent was evaporated. The residue was suspended in methanol (3 L) and stirred overnight. The suspension was chilled and then filtered. Solid obtained was dried under vacuum at 40° C. Yield 445 g (77%). 1HNMR(CDCl3): δ 9.94 (s, 1H), 7.86 (d, J=8.6 Hz, 2H), 7.80 (s, 1H), 7.28J=8.6 Hz, 2H), 7.11(d, J=2.9 Hz, 2H), 7.08(d, J=2.9 Hz, 2H), 6.36(t, J=2.2 Hz, 1H), 6.25 (d, J=2.2 Hz, 2H), 3.83(s, 3H), 3.63 (s, 6H).

Provenance & Evidence