Trolox → HCID 17840916, compound

Participants

Reaction Steps

To a solution of 5.47 g 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (21.9 mmol) in 170 mL THF was added 3.92 g CDI (24.2 mmol) and stirred for 1.25 h at room temperature. To this was added a solution of 2.14 g N,O-dimethylhydroxylamine hydrochloride (21.97 mmol) and 8.2 g N,N-diisopropylethylamine in 50 mL CH2Cl2 dropwise over 1 h. The reaction was stirred overnight, concentrated, 250 mL CH2Cl2 added and washed sequentially with 100 mL 0.625 M HCl, 100 mL 1.0 M NaHCO3 and 100 mL saturated NaCl. The organics were dried over Na2SO4, concentrated and purified by flash chromatography yielding 4.43 g of 6-hydroxy-N-methoxy-N,2,5,7,8-pentamethylchroman-2-carboxamide as an off-white crystalline solid.

Provenance & Evidence