Phenol → HCID 178426798, compound

Participants

Reaction Steps

To a solution of phenol (116 mg, 1.1 mmol) in THF (10 mL) was added 6,6-dimethyl-3-methanesulphonyl-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (0.2 g, 0.62 mmol) and NaOH (0.3 mL of a 4M solution, 1.1 mmol). The mixture was heated at reflux overnight. Phenol (50 mg, 0.62 mmol) and NaOH (0.15 mL of a 4M solution, 0.62 mmol) were then added and the mixture heated at reflux for an additional 8 h. The solution was cooled to room temperature, diluted with EtOAc (100 mL) and washed with NaOH (1M, 2×100 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with hexane:EtOAc (2:1) to give the title compound (35 mg, 18%) as a yellow solid. mp 232-234° C. 1H NMR (360 MHz, CDCl3) δ 1.10 (6H, s), 2.42 (2H, s), 2.86 (2H, s), 6.43 (1H, d, J=2.3 Hz), 7.20-7.26 (3H, m), 7.37 (1H, d, J=7.3 Hz), 7.39 (1H, d, J=8.7 Hz), 7.59 (1H, d, J=2.3 Hz). MS (ES+) 339 (M+1).

Provenance & Evidence