反应详情

A solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (500 mg, 2.0 mmol) in 10 mL THF was treated with 356 mg CDI (2.2 mmol). After 1 h, 366 mg 2-(2-methylaminoethyl)pyridine (3.0 mmol) in 10 mL THF was added over 1 h and stirred overnight. The solution was concentrated, dissolved into 70 mL CH2Cl2, extracted once with 1.0 M NaHCO3. The aqueous phase was then back extracted 2×25 mL CH2Cl2 and the combined organics washed with 2×25 mL saturated NaCl and dried over Na2SO4. The solution was concentrated and purified by flash chromatography to give 6-hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide.

1. concentrationThe solution was concentrated
2. dissolutiondissolved into 70 mL CH2Cl2
3. extractionextracted once with 1.0 M NaHCO3
4. extractionThe aqueous phase was then back extracted 2×25 mL CH2Cl2
5. washthe combined organics washed with 2×25 mL saturated NaCl
6. dry with materialdried over Na2SO4
7. concentrationThe solution was concentrated
8. custompurified by flash chromatography