Methanol → HCID 86665800, compound

Participants

Reaction Steps

A suspension of 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (10.0 g, 29 mmol) in methanol (200 mL) was added to a solution of potassium hydroxide (4.86 g, 87 mmol) in methanol (100 mL) under ice cooling. To the reaction mixture, diacetoxyiodobenzene (10.2 g, 32 mmol) was added in small portions for 5 minutes with the temperature kept at 5° C. or lower, and the reaction mixture was gradually warmed to room temperature and stirred for 1 day. Bisacetoxyiodobenzene (2.00 g, 6.2 mmol) was further added thereto at room temperature, and the mixture was stirred for 3 hours. Then, methanol was distilled off under reduced pressure. Water (100 mL) was added to the obtained concentrated residue, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained concentrated residue was suspended by the addition of diethyl ether (50 mL), and the resulting precipitate was collected by filtration, washed with diethyl ether (5 mL×2), and then dried under reduced pressure to obtain the title compound (RE8) (8.99 g, 76%) as a white powder.

Provenance & Evidence