Sodium Hydroxide → 4-Cyano-5-morpholin-4-ylthiophene-2-carboxylic acid

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Reaction Steps

To a solution of ethyl 4-cyano-5-morpholin-4-ylthiophene-2-carboxylate (0.06 g, 0.23 mmol) in THF/MeOH/water (3:1:1) (5 mL) was added sodium hydroxide (0.095 g, 2.3 mmol). The reaction mixture was allowed to stir at rt for 20 h and was concentrated. The residue was acidified to pH 1-2 with 1N HCl and was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated to give 4-cyano-5-morpholin-4-ylthiophene-2-carboxylic acid (0.048 g, 88%). LCMS: (FA) ES+ 239.1. 1H NMR (400 MHz, d6-DMSO) δ:7.67 s, 1H), 3.72-3.75 (m, 4H) and 3.52-3.55 (m, 4H).

Provenance & Evidence