Water → HCID 68905772, compound

Participants

Reaction Steps

Water (23 mL) was added to Compound 109 (11.8 g) dissolved in CH2Cl2 (120 mL) and the biphasic solution was stirred at room temperature. To this stirring solution was added DDQ (9.2 g) and the reaction mixture was stirred for 7 h at which point the reaction was complete. The reaction mixture was diluted with dichloromethane (500 mL) and it washed with 2% aqueous sodium bisulfite solution. The organic layer was separated and the aqueous layer was extracted several times with dichloromethane. The combined organic layer was washed with saturated sodium bicarbonate solution (5×300 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent removed under reduced pressure. The residue was purified by using 30% EtOAc in CH2Cl2 followed by 10% MeOH in CH2Cl2. Compound 110 obtained in a 96% yield as colorless pallets after removing the solvent.

Provenance & Evidence