4-(3-Phenylpropyl)pyridine N-oxide → HCID 86686866, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 4-phenylpropylpyridine-N-oxide (278 mg, 1.31 mmol) in methylene chloride (20 mL) was added (R,R)-Jacobsen catalyst (237.0 mg, 0.3732 mmol) and a solution of sodium hypochlorite (2.0 M in water; 16 mL, 32 mmol) at 0° C. The resulting brown suspension was stirred at 0° C. for 15 minutes then a solution of 6-chloro-1H-indene (1) (2.81 g, 18.6 mmol) in methylene chloride (20 mL) was added via syringe with simultaneous addition of additional sodium hypochlorite (2.0M in water; 16 mL, 32 mmol). The reaction was stirred at 0° C. for one hour then the ice bath was removed and the reaction was stirred at room temperature for 1 hr. An aliquot was taken and TLC on silica (hexanes) showed all starting material consumed. The reaction was poured into brine and extracted with methylene chloride. The combined extracts were washed with saline, then dried over sodium sulfate, filtered, and evaporated under reduced pressure to leave crude product which solidified when placed under hi-vacuum. Yield ˜3.7 g of a brown solid. 1H NMR (400 MHz, DMSO) δ 7.55 (d, J=7.6 Hz, 1H), 7.32 (s, 1H), 7.23 (d, J=7.3 Hz, 1H), 4.36 (s, 1H), 4.16 (s, 1H), 3.03 (dd, J=45.8, 18.2 Hz, 2H).

Provenance & Evidence