Water → HCID 118098694, compound

Participants

Reaction Conditions

Reaction Steps

To a partially dissolved mixture of 6A (7.00 g, 20.91 mmol) in DMSO (40 mL), was added sodium sulfide (3.26 g, 41.8 mmol). The mixture was stirred at 50° C. for 45 min. The reaction mixture was cooled to rt, poured into water (500 mL). The mixture was extracted with EtOAc (3×). The combined organic phase was washed with water and brine, filtered though a pad of SiO2 and concentrated to a red oil. The crude product was purified by flash chromatography (loaded in chloroform onto a 40 g column and eluted with a gradient from 0 to 100% ethyl acetate/hexanes). The desired fractions were collected, concentrated to give 6B (3.10 g, 9.33 mmol, 44.6% yield) as an orange solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.99 (d, J=7.15 Hz, 2H) 7.27-7.48 (m, 6H) 5.20 (br. s., 2H) 4.56 (br. s., 2H) 2.96 (br. s., 3H); MS (ESI) m/z: 333.1 [M+1]+.

Provenance & Evidence