Thionyl Chloride → HCID 57672390, compound

Participants

Reaction Conditions

Reaction Steps

To a dry, round bottom flask containing 13.4 (0.24 g, 0.88 mmol) under an argon atmosphere was added dry DCM (5 mL). The resulting homogeneous solution was cooled to 0° C. After 15 minutes, thionyl chloride (0.20 mL, 2.74 mmol) was added dropwise at 0° C. Upon complete addition of thionyl chloride, the mixture was allowed to warm to room temperature and for 16 hours. After 19 hours, the solvent was removed under reduced pressure. The crude material was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 15% EtOAc in hexanes) to yield a colorless oil 13.5 (0.13 g, 49% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.36 (2H, dd, J=8.2, 2.0 Hz), 7.13 (1H, m), 6.98 (1H, d, J=8.2 Hz), 6.93 (2H, m), 4.62 (2H, s), 3.84 (3H, s), 1.87 (1H, m), 0.91 (2H, m), 0.7 (2H, m).

Provenance & Evidence