Sodium Hydroxide → (E)-(S)-3-{4-[3-(4'-chloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid

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Reaction Steps

Sodium hydroxide (1M, 2.3 ml, 2.3 mmol) was added to a solution of (E)-(S)-ethyl 3-{4-[3-(4′-chloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (example 52) (0.600 g, 1.25 mmol) in ethanol (10 ml) and the mixture stirred at room temperature for 18 h, then heated to 80° C. for 2 h. The resulting mixture was partitioned between water (50 ml) and ethyl acetate (50 ml) and the aqueous layer acidified to pH1 by addition of 1N HCl. The aqueous layer was separated and further extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine, dried (MgSO4), evaporated, and the product and vacuum dried at 40° C. for 72 h, to give (E)-(S)-3-{4-[3-(4′-chloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid as a colourless solid; 0.53 g (94%).

Provenance & Evidence