HCID 53989278, compound → HCID 9884959, compound

Participants

Reaction Steps

The above ethyl ester 11 (712 mg, 2.18 mmol) in 35 mL MeOH was hydrolyzed as described for Example 1 to give the crude acid. The crude mixture was purified by HPLC (80% MeOH/20% 10 mmol NH4OAc+0.3% AcOH) to give 390 mg (60%) of pure (2E, 4E)-6-[1-(3,4-diethylbenzene)-cyclopropyl]-3-methyl-2,4-hexadienoic acid (12). 1H NMR (400 MHz, CDCl3) δ7.04 (m, 3H, aromatic), 6.15 (dt, J=15.6 and 6.8 Hz, 1H, vinylic CH), 6.05 (d, J=15.6 Hz, 1H, vinylic CH), 5.69 (s, 1H, vinylic CH), 2.62 (q, J=7.5 Hz, 4H, aliphatic 2CH2), 2.43 (d, J=6.8 Hz, 2H, allylic CH2), 2.23 (s, 3H, aliphatic CH3), 1.20 (m, 6H, aliphatic 2CH3), 0.84 (dd, J=6.2, 4.7 Hz, 2H, aliphatic CH2), 0.73 (dd, J=5.4, 4.1 Hz, 2H, aliphatic CH2).

Provenance & Evidence