Sodium Hydroxide → (2Z,4E,6E)-2,6-Difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid

Participants

Reaction Steps

Following General Procedure E and using (2Z,4E,6E)-2,6-difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester (Compound 20, 314 mg, 0.66 mmol), 1M NaOH (2.0 mL) and EtOH (5 mL) at 40° C. for overnight followed by flash column chromatography on silica gel (10%→50% EtOAc-hexane), the title compound was obtained as a yellow solid (282 mg, 95%). 1H NMR (300 MHz, CDCl3): δ0.98 (t, J=7.6 Hz, 3H), 1.23 (s, 6H), 1.29 (s, 6H), 1.67 (s, 4H), 2.06 (d, J=3.2 Hz, 3H), 2.47 (m, 1H), 2.68 (m, 1H), 3.44 (s, 3H), 5.12 (s, 2H), 6.35 (dd, J=26.1, 15.8 Hz, 1H), 6.94 (s, 1H), 7.01 (dd, J=15.8, 1.8 Hz, 1H), 7.02 (s, 1H).

Provenance & Evidence