Hexane → HCID 86728094, compound

Participants

Reaction Conditions

Reaction Steps

A 100 ml RBF was charged with 2-methyl-2-(methylsulfonyl)propanenitrile (1.028 g, 6.99 mmol) and THF (15 ml). The solution was cooled to −78° C. (dry ice-acetone bath) and to it a butyllithium solution, 1.6 m in hexane (4.66 ml, 6.99 mmol) was added dropwise. The mixture was stirred for 20 min at −78° C. In the separate 50 ml flask solution of N-(1-(2-fluoro-5-nitrophenyl)ethylidene)-2-methylpropane-2-sulfinamide (1.00 g, 3.49 mmol) in toluene (10 ml) was cooled to −78° C. (dry ice acetone bath) and trimethylaluminum (2M in heptane) (1.921 ml, 3.84 mmol) was added. The mixture was stirred for 5 min, then transferred via syringe to the solution of the metallated sulfone (dropwise addition at −78° C.). The mixture was stirred for 1 hr at −78° C. The reaction mixture was quenched by addition of 1 ml saturated aqueous solution of Na2SO4 and the flask was removed from the bath, stirred for 40 min and diluted with 5 ml EtOAc. After filtering through pad of celite organic fractions were separated, concentrated and purified by FC on 12 g RediSep Gold column using 10-80% EtOAc in heptane to give desired N-(1-((2-cyanopropan-2-yl)sulfonyl)-2-(2-fluoro-5-nitrophenyl)propan-2-yl)-2-methylpropane-2-sulfinamide (0.902 g, 2.081 mmol, 59.6% yield).

Provenance & Evidence