Hydrochloric Acid → HCID 22010142, compound

Participants

Reaction Steps

A solution of (RS)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(2-methyl-5-(2-(trimethylsilyl)ethoxymethoxy)phenyl)butanoic acid (1.8 g) in tetrahydrofuran (150 mL) is treated with 1 N hydrochloric acid (10 mL) and the mixture heated at reflux for 1 hour. The reaction mixture is evaporated and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The organic phase is washed with water (100 mL), brine (100 mL), dried over magnesium sulphate and evaporated. The residual brown gum (1.25 g) is recrystallised from acetonitrile to give (RS)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(5-hydroxy-2-methylphenyl)butanoic acid (0.5 g) as a cream solid, m.p. 198-200° C. [Elemental analysis:- C,68.32; H,5.45; N,6.93%. Calculated:- C,68.89; H,5.30; N,6.69%]

Provenance & Evidence