Toluene → HCID 11645176, compound

Participants

Reaction Steps

An oven dried, nitrogen cooled two-necked 25 mL round bottom flask was charged with a solution of 78 μL piperidine (0.793 mmol, 68 mg) in 4.0 mL anhydrous DCM. Trimethyl aluminum was added slowly (2.0M/toluene, 436 μL, 0.872 mmol). The resulting mixture was stirred for twenty minutes at room temperature. To this solution was added 200 mg of the diester 3 (0.793 mmol) dissolved in 2.0 mL anhydrous DCM. The flask was sealed and heated to 41° C. for 15 hours. The reaction was allowed to cool to room temperature and quenched with slow addition of 1M HCl. The product was extracted three times with DCM, the organic fractions collected, washed with brine, dried over magnesium sulfate and evaporated to give a brownish/yellow oil. The crude mixture was applied to a column of silica gel and eluted with a 2:1 hexane-ethyl acetate solution (Rf=0.16) to give 132 mg of product (54% yield) as a yellow oil. MS: (ESI-TOF) MH+ expected: 306.1812, found: 306.1807.

Provenance & Evidence