Diethyl Ether → HCID 86638344, compound

Participants

Reaction Steps

To a solution of 288 (766 mg, 1.599 mmol) in DCM (10 mL) at 0° C. was added DIBAL (3.2 mL, 3.2 mmol, 1.0M in DCM). The reaction mixture was gradually warmed to RT overnight. LCMS indicated incomplete conversion. Additional DIBAL (3.2 mL, 3.2 mmol) was added and the reaction mixture was stirred for an additional 5 h. The reaction mixture was cooled to 0° C. and diluted with ether (20 mL). The reaction was quenched by careful addition of 6N HCl (1.5 mL). The resulting suspension was extracted with EtOAc and the organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatograph eluting with an EtOAc/hexane gradient (20% to 30% EtOAc) to afford 263 mg (34%) of N-{4-[2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-1-formyl-1-methyl-ethyl]-phenyl}-methanesulfonamide (292) as a tan oil.

Provenance & Evidence