Ethanolamine → HCID 67262915, compound

Participants

Reaction Steps

6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (5.00 g 19.98 mmol) in 150 mL THF was treated with 3.65 g CDI (22.5 mmol) and the exothermic reaction let stir for 1 h at room temperature. Ethanolamine (1.35 g, 22.10 mmol) in 50 mL THF was added over 1 h and the solution stirred overnight. The reaction was concentrated, dissolved into 375 mL CH2Cl2 and washed with 250 mL 0.1 M HCl, 250 mL 0.5 M NaHCO3, 2×100 mL saturated NaCl and dried over Na2SO4. The acidic aqueous phase was extracted 3×100 mL CH2Cl2 and washed with 50 mL saturated NaCl and dried over Na2SO4. The combined organics were concentrated and purified by flash chromatography yielding 2.88 g of 6-hydroxy-N-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman-2-carboxamide as an off white impure solid.

Provenance & Evidence