Sodium Hydroxide → 2-Ethoxy-3-(4-(4-(4-(2-ethoxy-2-hydroxycarbonyl-ethyl)-phenyloxy)-but-2-enyloxy)-phenyl)-propionic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-ethoxy-3-(4-(4-(4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenyloxy)-but-2-enyloxy)-phenyl)-propionate (0.210 mmol, 109 mg) was dissolved in ethanol (7 ml) by heating to 60° C. 1M NaOH (2.3 ml) was added and the reaction mixture was stirred at 90° C. for 90 min. The reaction mixture was evaporated and 1 N HCl (6.5 ml) and methylene chloride (30 ml) was added to the residue. The organic phase was collected and the aqueous phase was further extracted with methylene chloride (2×25 ml). The combined organic phases were dried and evaporated to give the title compound in 87 mg (88%) yield. 1H-NMR δ (CDCl3) 9.55 (br. s, 2H), 7.17 (d, 4H), 6.80 (d, 4H), 5.91 (m, 2H), 4.65 (d, 4H), 4.05 (m, 2H), 3.70-3.57 (m, 2H), 3.50-3.35 (m, 2H), 3.10-2.90 (m, 4H), 1.21 (t, 6H).

Provenance & Evidence