4-Nitrobenzoyl chloride → 3-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoate

Participants

Reaction Steps

To a stirred solution of 3-(trifluoromethyl)-1-(trimethylsilyl)pent-1-yn-3-ol (10.5 g, 46.9 mmol) in DMF (140 mL), sodium hydride (60% in oil, 1.9 g, 46.9 mmol) was added portionwise. After 25 min stirring, a solution of 4-nitrobenzoyl chloride (8.7 g, 46.9 mmol) in 50 mL DMF was added slowly. The reaction mixture was then stirred at room temperature for 2 hours. The reaction mixture was quenched with pH 7 buffer 25% NH4OAc aq solution (500 mL) and the product was extracted with diethyl ether (4×), washed with water (3×) and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (Ethyl acetate/hexanes, 15:85). 1H NMR (400 MHz, acetone-d6): 8.45 (d, 2H), 8.27 (d, 2H), 3.69 (s, 1H), 2.60-2.40 (m, 2H), 1.16 (t, 3H).

Provenance & Evidence