Water → HCID 66696588, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 1B (1.01 g, 4.12 mmol) in tetrahydrofuran (20 mL) was cooled to −78° C., then lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 4.6 mL, 4.6 mmol) was added slowly. The reaction was allowed to stir at −78° C. for 20 minutes, and then hexachloroethane (1.95 g, 8.23 mmol) was added all at once. The reaction was allowed to warm to room temperature, and stir overnight. After this time, the reaction mixture was poured into water and extracted with ether. The extracts were dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel (eluant of 100% hexane, then gradient to 15% ethyl acetate-hexane) to yield the title compound as a white solid (780 mg, 68% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.91 (m, 1H), 7.66 (m, 2H), 2.42 (s, 3H).

Provenance & Evidence