Triethylborane → HCID 22911977, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the methyl sulfone (Example 16) (0.21 g, 0.47 mmol) in tetrahydrofuran (THF) (5 mL) at 0° C. under nitrogen was added 2M n-butyl magnesium chloride in THF (1.0 mL, 2.0 mmol) slowly, via syringe, and the mixture stirred at 0° C. for 30 minutes and then at room temperature (25° C.) for 2 hours. After cooling to 0° C., a 1.0M solution of triethyl borane in THF (2.5 mL, 2.5 mmol) was added and the mixture warmed to room temperature and stirred for 2 hours, and then heated to reflux overnight (18 hours). After cooling to room temperature and stirring for 3 hours, water (3 mL) was added followed by sodium acetate (1.2 g) and hydroxylamine-O-sulfonic acid (0.82 g). After stirring at room temperature overnight, the mixture was poured into 3 volumes of ethyl acetate, and the organic layer washed with water and brine and dried over MgSO4. After solvent removal, the white solids (a mixture of product and starting material) was recrystalized from ethyl acetate/hexane to provide 0.11 g of a white solid. Anal. Calc'd for C21H14N2O2S2FCl: C, 56.69; H, 3.17; N, 6.30. Found: C, 55.99; H, 2.97; N, 6.15.

Provenance & Evidence