Hydrochloric Acid → 8-(1,3-Dimethoxypropan-2-yloxy)-2-methylquinoline

Participants

Reaction Steps

To a solution of 2-methylquinolin-8-ol (4.10 g, 25.76 mmol), PPh3 (16.89 g, 64.39 mmol) and 1,3-dimethoxypropan-2-ol (4.02 g, 33.48 mmol) in THF (20 mL) was added DIAD (8.40 mL, 41.21 mmol) dropwise at ambient temperature. The reaction mixture was stirred at room temperature for two days. 4 N HCl (7.73 mL, 30.91 mmol in water), water (20 mL), and ethyl acetate (50 mL) were added. The aqueous layer was separated and washed with ethyl acetate. The aqueous layer was neutralized with ammonium hydroxide to about pH 9 and extracted with ethyl acetate (50 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:2 hexane/ethyl acetate) to give 8-(1,3-dimethoxypropan-2-yloxy)-2-methylquinoline (6.00 g, 89.15%) as an oil.

Provenance & Evidence