Sodium Hydroxide → HCID 58968947, compound

Participants

Reaction Steps

To a solution of 2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester (4.12 g, 8.35 mmol) in THF/MeOH (50/10 mL) was added 2 N NaOH (16 mL). After 1.5 h, added an additional 5 mL of 3 N NaOH. After another 1 h, added an additional 16 mL of 2 N NaOH, and stirred overnight. The solution was diluted with EtOAc (100 mL) and H2O (100 mL) and washed with EtOAc. The aqueous fractions were acidified with 5% citric acid, and extracted with EtOAc. The combined organic fractions were dried, filtered, and concentrated to yield the desired acid, which was used without further purification. MS (EI): cal'd (M−), 478.1, exp (M−), 478.6.

Provenance & Evidence