4-Nitrobenzoyl chloride → HCID 59774865, compound

Participants

Reaction Steps

A solution of crude 1,1,1-trifluoro-2-methyl-4-(trimethylsilyl)but-3-yn-2-ol from Step 1 (˜20.2 mmol) in DMF (10 mL) was added dropwise to a suspension of NaH (60% disp., 850 mg, 21.2 mmol) in DMF (25 mL) at 0° C. The mixture was allowed to reach room temperature, stirred for 30 min. and recooled to 0° C. A solution of 4-nitrobenzoyl chloride (3.94 g, 21.2 mmol) in DMF (10 mL) was added dropwise and the resulting mixture was stirred at room temperature. After 30 min., the mixture was poured in 1:1 25% NH4OAc/H2O and extracted with Et2O (3×). The combined organic layers were washed with H2O (3×) and brine, dried (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (toluene/hexane 40:60 to 60:40) affording the title compound. 1H NMR (400 MHz, acetone-d6): 8.44 (d, 2H), 8.28 (d, 2H), 3.65 (s, 1H), 2.09 (s, 3H).

Provenance & Evidence