Sodium Hydroxide → Ethyl hydrogen (E)-2-{4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate

Participants

Reaction Steps

To a solution of diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate (63) (0.051 g, 0.115 mmol) in EtOH (4 mL) was added aqueous NaOH (1 mL of a 5M solution, 5 mmol). The solution was heated to reflux for 4 h, then cooled to RT and concentrated. The residue was dissolved in water (1 mL) and the pH adjusted to ˜2 with 1 N aqueous HCl. The mixture was extracted with EtOAc (2×10 mL). The organics were dried (Na2SO4) and concentrated to provide compound 64 (0.041 g, 86%) as a waxy yellow solid. 1H NMR (DMSO-d6): δ 9.28 (s, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.20 (dd, J=22.0 Hz, 17.6 Hz, 1H), 7.10 (d, J=8.1 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.41 (t, J=17.6 Hz, 1H), 3.90-3.84 (m, 2H), 2.20 (m, 4H), 1.50 (m, 8H), 1.18 (t, J=6.9 Hz, 3H). LRMS (ESI): m/z 411 (M−H)−.

Provenance & Evidence