Hexachloroethane → HCID 66696678, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 33A (0.94 g, 4.8 mmol) in THF (20 mL) was cooled to −78° C., then treated slowly with LiHMDS (1M in THF, 6.3 mL, 6.3 mmol). The reaction was stirred at −78° C. for 20 min and then treated all at once with solid hexachloroethane (2.31 g, 9.75 mmol). The flask was removed from the cold bath, and the reaction mixture was allowed to stir overnight at room temperature. After this time, it was poured into water and extracted with Et2O. The combined Et2O extracts were concentrated in vacuo, and the residue was chromatographed on silica gel (Analogix® SF25-60 column; 100% hexane for 10 minutes, then 0% to 15% EtOAc/hexanes over 10 minutes) to afford 0.673 g (61%) of the title compound as a bright yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 7.17 (d, J=3.6, 1H), 6.93 (dt, J=3.7, 1.0 1H), 2.86 (qd, J=7.6, 1.0 2H), 2.27 (s, 3H), 1.26 (t, J=7.5, 3H). MS (DCI+) m/z 228 (M+H).

Provenance & Evidence