Ethyl Acetate → HCID 42599387, compound

Participants

Reaction Steps

To a solution of N-(3-(1H-imidazol-1-yl)propyl)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (100.7 mg, 0.282 mmol) in 6 mL AcCN and 6 mL CH2Cl2, cooled to 0° C., was added a cooled solution of CAN (340 mg, 0.620 mmol) in 2 mL H2O, dropwise over 5 minutes. The reaction was immediately treated with 5 mL EtOAc and washed 3×3 mL H2O. The aqueous layer was basified with 6 mL saturated NaHCO3 solution and extracted 6×3 mL EtOAc. The combined organics were dried over Na2SO4 and concentrated to a yellow oil. Flash chromatography yielded 98.1 mg of N-(3-(1H-imidazol-1-yl)propyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Provenance & Evidence