Thiophenol → HCID 178516060, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask containing thiophenol (30 μl, 0.29 mmol), cesium fluoride (44 mg, 0.29 mmol) and N,N-dimethylformamide (3 ml) was warmed at 40° C. for 1 hr. To this was added cis-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl methanesulfonate (100 mg, 0.19 mmol) in N,N-dimethylformamide (1 ml) and the reaction mixture stirred at 50° C. for 18 hr. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with brine (10 ml), dried over magnesium sulfate and concentrated in vacuo. Purification via flash column chromatography (SiO2, ethyl acetate/petrol, 1:3) afforded the title compound (23 mg, 40%) as an off-white solid. δH (d4-MeOH) 1.40-1.57 (4H, m), 1.82-1.90 (2H, m), 2.04-2.16 (2H, m), 2.80 (1H, m), 3.13 (1H, m), 6.19-6.28 (2H, m), 6.88 (1H, d), 7.23 (1H, m), 7.30 (2H, m), 7.40 (2H, m); m/z (ES+) 301 (M+H)+.

Provenance & Evidence