Water → 2-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)quinoline

Participants

Reaction Steps

8.6 g (35 mmol) of 2-phenyl-3-methyl-8-vinylquinoline are added, at 0° C., to a suspension of 52 g of AD-mix-α in a mixture of 200 ml of distilled water and 200 ml of tert-butanol. The reaction mixture is then vigorously stirred for 16 hours at this same temperature using a mechanical stirrer. 2 g of Na2SO3 are then added. The reaction mixture is stirred for one hour and is then taken up in 200 ml of water and extracted with 3×200 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to provide 6.65 g of 2-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)quinoline in the form of an orange-colored solid; M.p.=117° C. (Yield: 69%)

Provenance & Evidence