Sodium Hydroxide → HCID 69060272, compound

Participants

Reaction Steps

To a solution of methyl 3-cyano-3-phenylhex-5-enoate (6.03 g, 26.3 mmol) in methanol (90 mL) was added 1M aqueous NaOH (29 mL, 29 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated under vacuum. The residue was partitioned between EtOAc and water and the pH of the aqueous phase was adjust to pH 4 using 3N aqueous HCl. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 12.45 (br, 1H), 7.50 (d, J=1.6 Hz, 2H), 7.45 (t, J=1.9 Hz, 2H) 7.42 (t, J=1.7 Hz, 1H), 5.51 (m, 1H), 5.11 (m, 2H), 3.17 (s, 2H), 2.77 (m, 2H), 2.51 (s, 2H) ppm. ES MS M+1=216.

Provenance & Evidence