Dichloromethane → HCID 22254567, compound

Participants

Reaction Steps

To a 100 mL round bottom flask charged with 2 mL of CH2Cl2, 0.500 g (2.07 mmol) of 8-(1,3,3-trimethylbutoxy)quinoline was slowly added with gentle heating in order to dissolve the material. To this was added 1.8 equiv m-CPBA (50–70% by weight) in three portions. After stirring for 30 min, the dense solution became a brown solid. The solid was dissolved in 25 mL EtOAc and the resulting solution was washed with 10% aqueous NaHSO3, saturated aqueous NaHCO3, and the organic layer evaporated in vacuo. After co-evaporation with toluene, the residue was dissolved in POCl3 (5 mL) and the flask fitted with a reflux condenser. The reaction flask was then placed in an oil bath that had been preheated to 95° C. for 15 min. After cooling to room temperature, the solution was concentrated down to a red oil, which was then dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 until the aqueous layers became basic. The organic layer was evaporated in vacuo and the residue was purified by silica gel column chromatography (EtOAc/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.37 (d, 1H), 7.55 (m, 3H), 7.34 (m, 1H), 4.70–4.93 (m, 1H), 1.90 (dd, 1H), 1.53 (dd, 1H), 1.30 (d, 3H), 0.94 (s, 9H); MS (DCI/NH3) m/z 277 [M+H]+.

Provenance & Evidence