Hydrochloric Acid → HCID 57446112, compound

Participants

Reaction Steps

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%).

Provenance & Evidence