Iodoethane → HCID 117701588, compound

Participants

Reaction Steps

To a solution (suspension) of 7-hydroxy-3,8-dimethyl-2-[(2R)-pyrrolidin-2-yl]-4H-chromen-4-one hydrochloride (78 mg, 0.30 mmol) obtained in Example 2-3 and 2,6-lutidine (52 μL, 0.45 mmol) in dimethylformamide (1.5 mL), iodoethane (31 μL, 0.39 mmol) was added dropwise under cooling with ice, and then the mixture was brought back to room temperature and stirred for 6.5 hours. 2,6-Lutidine (105 μL, 0.90 mmol) was added to the reaction solution, and the mixture was cooled with ice again. Then, acetyl chloride (43 μL, 0.60 mmol) was added dropwise thereto, and the mixture was brought back to room temperature and stirred overnight. The reaction solution was concentrated, and then a saturated aqueous solution of sodium bicarbonate was added to the obtained residue, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→90/10) to obtain 58 mg of the title compound (yield: 59%).

Provenance & Evidence