Ethyl Acetate → HCID 67979386, compound

Participants

Reaction Steps

6″-Bromodispiro[1,3-dioxolane-2,1′-cyclohexane-4′,2″-inden]-1″(3″H)-one (Intermediate 71, 320 mg, 0.95 mmol), 2-methylpropane-2-sulfinamide (173 mg, 1.42 mmol) and titanium ethoxide (0.391 mL, 1.90 mmol) were dissolved in 2-Me THF (5 mL) and heated to reflux overnight. The reaction was stopped and was left to cool down to r.t. EtOAc and water were added under stirring. The mixture was left to stand still for 2 h. The organic phase was collected by filtration, dried using a phase separator and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient of 0-30% EtOAc in heptane to give the title compound (290 mg, 69% yield): 1H NMR (500 MHz, CDCl3) δ ppm 1.35 (s, 9 H) 1.48-1.54 (m, 1 H) 1.61 (dd, 1 H) 1.67-1.77 (m, 2 H) 1.81-1.90 (m, 2 H) 2.10 (br. s., 2 H) 2.95-3.05 (m, 2 H) 3.95-4.02 (m, 4 H) 7.25 (s, 1 H) 7.60 (dd, 1 H) 8.62 (br. s., 1 H); MS (ES+) m/z 440.0 [M+H]1.

Provenance & Evidence