Methane, dichloromethoxy- → HCID 21931734, compound

Participants

Reaction Steps

To a flame dried round bottom flask equipped with a nitrogen cap was added 89 mg (66 mmol) aluminum chloride and 5 ml of methylene chloride (CHCl2). The mixture was stirred at ambient temperature for 0.25 hour and then cooled to 0° C. followed by the addition of 75 mg (0.34 mmol) 6-methoxy-1,4,4-trimethyl-3,4-dihydro-1H-quinolin-2-one. The reaction mixture was stirred for 10 minutes at this temperature and was then treated with 84 μl (0.93 mmol) of α,α-dichloromethyl methyl ether before allowing the reaction to slowly warm to room temperature over 16 hours. The reaction mixture was quenched with 30 ml of 2M HCl and extracted with ethyl acetate (3×30 ml). The combined organics were then washed with saturated aqueous bicarbonate solution and brine followed by drying over sodium sulfate and evaporation in vacuo. The crude residue was purified on silica gel eluting with 1:1 ethyl acetate/hexane to afford two products. The more polar material was identified as the desired product: Mass spectrum APCI m/e 248 (p+1). The less polar product was identified as 7-Dichloromethyl-6-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (Mass spectrum APCI m/e 302 (p+1)) from which the desire product was isolated after a brief stirring in pH 7 phosphate buffer. Total yield 56 mg (66%).

Provenance & Evidence