Water → 3-(Quinolin-2-ylmethoxy)-propan-1-ol

Participants

Reaction Conditions

Reaction Steps

1,3-Propanediol (6.0 mL, 85 mmol) is dissolved in 20% DMPU in THF (80 mL) and cooled to 0° C. Sodium hydride (60%, 3.6 mg, 90 mmol) is added portionwise, and the contents are allowed to stir for 15 min. at 0° C. 2-Chloromethylquinoline (7.64 g, 42.7 mmol) is added and the reaction is allowed to stir overnight. The reaction is poured into water (700 mL) and extracted with ethyl acetate (1×200 mL). Sodium chloride is added to the aqueous layer and extracted again with ethyl acetate (2×200 mL). The organic layers are pooled and washed with water (2×300 mL) and brine (2×300 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material is purified by flash chromatography (silica, 2.5% methanol in dichloromethane) to give the title compound. MS (ESI) 218 (M+H)+.

Provenance & Evidence