Potassium Hydroxide → HCID 20147168, compound

Participants

Reaction Steps

Diethyl 2-[3-(1-tridecynyl)-4-pyridyl]methylenepropane-1,3-dioate (0.47 g, 1.1 mmole, from Example 3) was added to a solution of potassium hydroxide (0.66 g) in water (7.5 ml) and the mixture was heated to reflux for 24 hours. The resulting clear solution was then acidified at 0° C. and the precipitated product was filtered off and washed with water. Recrystallisation of the dried material from ethyl acetate gave 1.37 g (34%) of the title compound, mp 175°-177° C., νmax (mull) 2500 (broad), 1740 cm-1 ; δ(DMSO) 0.84 (3H, distorted t, terminal CH3), 1.20 (14H, m, alkylene chain), 1.42 (2H, m, CH2 (CH2)2C≡C), 1.57 (2H, m, CH2CH2C≡C), 2.50 (2H, t, CH2C≡C), 7.41 (2H, d, J 5.1 Hz, C-5H), 7.74 (1H, s, Ar CH=C), 8.56 (1H, d, J 5.1 Hz, C-6H), 8.67 (1H, d, J 0.5 Hz, C-2H), 13.73 (2H, broad exchangeable, CO2H).

Provenance & Evidence