Pivaloyl chloride → HCID 25130825, compound

Participants

Reaction Steps

To a suspension of 16z (0.50 g, 1.1 mmol) in DCM (55 mL) was added TEA (395 μL, 2.84 mmol). Pivaloyl chloride (174 μL, 1.42 mmol) was then added to the suspension in one portion and the reaction mixture was stirred at room temperature for 10 min at which time TLC indicated reaction completion. The reaction mixture was washed with cold water and extracted with DCM (2×). The organic layer was dried over anhydrous sodium sulfate and filtered and DCM was removed in vacuo. The resulting solid was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 eluent) to yield 17z as a light orange powder (0.34 g, 66%). Mp decomposition at 192° C. 1H NMR (400 MHz, CDCl3): δ 7.72 (d, J=2.8 Hz, 1H), 7.13 (dd, J=8.8 Hz, 2.8 Hz, 1H), 6.88 (d, J=8.8 Hz, 1H), 3.90 (s, 3H), 2.79 (q, J=7.6 Hz, 2H), 2.30 (s, 3H), 1.39 (s, 9H), 1.34 (t, J=7.6 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 178.6, 164.6, 164.2, 163.8, 162.2, 149.1, 144.9, 128.9, 125.5, 120.5, 113.8, 112.3, 104.9, 56.3, 40.1, 26.7, 21.4, 13.5, 12.2. HRMS m/z (ESI) calcd. for C21H25ClN4O2S2 (M+H)+ 465.1180. Found 465.1181.

Provenance & Evidence