Sodium Chloride → HCID 42599641, compound

Participants

Reaction Steps

To a solution of 100 mg (0.266 mmol) of 6-hydroxy-2,5,7,8-tetramethyl-N-(3-morpholinopropyl)chroman-2-carboxamide in 5 mL AcCN and one drop of H2O at 0° C., was added a solution of 320.3 mg CAN (0.584 mmol) in 3 mL H2O dropwise. The solution was treated with 5 mL EtOAc and 5 mL saturated NaCl followed by ˜1 g of NaHCO3 and 1 h of vigorous stirring. The suspension was then extracted 3×5 mL 4:1 isopropyl alcohol:isopropyl acetate solution and the combined organics dried over Na2SO4, concentrated to a yellow oil and flashed chromatographed to yield 16 mg of 2-hydroxy-2-methyl-N-(3-morpholinopropyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a dark yellow oil.

Provenance & Evidence