HCID 53989278, compound → HCID 9884959, compound

Participants

Reaction Steps

The above ethyl ester 11 (33 mg, 0.09 mmol) in 1.5 mL MeOH was hydrolyzed as described for Example 1 to give the crude acid. The crude mixture was purified by HPLC (82% MeOH/18% 10 mmol NH4OAc+0.3% AcOH) to give 14 mg (45%) of pure (2E, 4E)-6-[1-(3,5-di-t-butyl phenyl)-cyclopropyl]-3-methyl-2,4-hexadienoic acid (12). 1H NMR (400 MHz, CDCl3) δ7.24 (d, J=2.8 Hz, 1H, aromatic), 7.10 (d, J=1.8 Hz, 2H, aromatic), 6.17 (dt, J=15.6 and 7.0 Hz, 1H, vinylic CH), 6.03 (d, J=15.6 Hz, 1H, vinylic CH), 5.68 (s, 1H, vinylic CH), 2.41 (d, J=7.0 Hz, 2H, allylic CH2), 2.24 (s, 3H, aliphatic CH3), 1.31 (s, 18H, aliphatic 6CH3), 0.88 (dd, J=11.2, 7.1 Hz, 2H, aliphatic CH2), 0.74 (dd, J=10.2, 4.1 Hz, 2H, aliphatic CH2).

Provenance & Evidence