Sodium Hydroxide → 3-(4-Tert-butylbenzenesulfonamido)thiophene-2-carboxylic acid

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Reaction Steps

To a solution of 55 (0.817 g; 2.31 mmol) in methanol (4.5 mL) was added aqueous sodium hydroxide (9.2 mL; 1N). After the reaction was complete, the mixture was partitioned between diethyl ether and water; the organic layer was separated and set aside. The aqueous layer was acidified with excess aqueous hydrochloric acid (2N) and extracted with ethyl acetate (2×). The diethyl ether and ethyl acetate organic layers were combined, dried over sodium sulfate, decanted, and concentrated under reduced pressure. The resulting residue yielded the desired product a white solid from a mixture of hexanes and dichloromethane (0.54 g).

Provenance & Evidence