1,2-Dimethoxyethane → HCID 59192511, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of trifluoro-methanesulfonic acid 8-oxo-4-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-2-yl ester (XXVII, 542 mg, 1.23 mmol) and cesium carbonate (599 mg, 1.84 mmol) was added dimethoxyethane (11 mL) at room temperature. The resulting brown suspension was then heated at 80° C. and stirred for 3 h. The reaction mixture was cooled to room temperature and diluted with saturated ammonium chloride solution (50 mL), and then extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The crude product was dissolved in dichloromethane (15 mL) and diluted with hexanes (100 mL), then heated to remove the dichloromethane. The cloudy solution was then stored in the refrigerator for 15 h. The resulting solids were collected by filtration and washed with hexanes. After drying in the air, trifluoro-methanesulfonic acid 4-hydroxy-8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (182 mg, 51%) was obtained as a dark brown solid: ES(−)-HRMS m/e calcd. for C11H9F3O5S (M−H)− 309.0050, obsd. 309.0049.

Provenance & Evidence