反应详情

To a stirring solution of NaOH in MeOH (2.5 M, 18.8 mL) and DMF (60 mL) was added 1 (4.33 g, 18.8 mmol). The mixture was allowed to stir for 45 min at 23° C. before propargyl bromide (80% in PhMe, 3.36 mL, 22.56 mmol) was added slowly over 10 min. After 2.5 h, an aqueous solution of 1 M HCl was added to achieve pH=6, where upon a white precipitate forms. Water was then added and the organic layer was extracted 3×EtOAc and the combined organic extracts washed 1×H2O, 1× brine, and then dried over MgSO4. The solvents were removed in vacuo and the crude residue purified by flash chromatography using Hexanes:EtOAc on a Biotage purification system to yield 3 as a pale yellow solid (1.43 g, 29%).

1. additionwas added slowly over 10 min
2. extractionthe organic layer was extracted 3×EtOAc
3. washthe combined organic extracts washed 1×H2O, 1× brine
4. dry with materialdried over MgSO4
5. customThe solvents were removed in vacuo
6. customthe crude residue purified by flash chromatography
7. customEtOAc on a Biotage purification system