Periodate → 2-[8-(Benzyloxy)quinolin-7-yl]-1-phenylethanol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-[8-(benzyloxy)quinolin-7-yl]propane-1,2-diol (8.08 mmol) in tetrahydrofuran (60 mL) and water (20 mL) in a round bottom flask was added sodium (meta)periodate (8.08 mmol, 1.0 eq.) all at once and the resulting solution was stirred for 30 min. The tetrahydrofuran was then removed by rotary evaporation at room temperature (elevated temperatures will result in decomposition of the product) and the resulting heterogeneous mixture was diluted with water (40 mL) and washed with diethyl ether (2×50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated (at room temperature) to give the product as a pale yellow oil that was analytically pure and used directly in the ensuing step. (Caution: Compound decomposes rapidly at temperatures greater than 25° C., in the presence of silica gel, and potentially if brought to dryness in presence of periodate salts present in crude reaction mixture.) To a stirring solution of the (8-benzyloxy-quinolin-7-yl)-acetaldehyde (8.08 mmol, 1.0 eq.) from the initial step in tetrahydrofuran (10 mL) at −78° C. was dropwise added a 1M solution of phenylmagnesium bromide in THF (8.08 mmol, 1.0 eq.). On completion of addition, the reaction mixture was allowed to stir at −78° C. for 1 h and was then warmed to room temperature and stirred 30 min. The reaction was then quenched by addition of saturated aqueous sodium bicarbonate solution (5 mL) and allowed to stir for 5 min. The resulting solution was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated to give a thick yellow syrup that was purified by column chromatography using 20% ethyl acetate/hexanes to give the final product as a pale yellow solid (2.72, 34% for 2 steps). MS (ESI) m/z 356.3; HRMS: calcd for C24H21NO2+H+, 356.16451; found (ESI-FTMS, [M+H]1+), 356.16552.

Provenance & Evidence