Methyl 5-(hydroxymethyl)-3-phenylthiophene-2-carboxylate → 5-(Methoxycarbonyl)-4-phenylthiophene-2-carboxylic acid

Participants

Reaction Steps

To a solution of 169 (1.20 g, 4.83 mmol) in 30 mL of acetone was added dropwise Jones reagent (5 mL, 1.3M, 6.5 mmol) and stirred at room temperature for 1 hour. The reaction mixture was quenched with 10 mL of IPA, stirred for 10 min, filtered over a pad of Celite®. The filtrate was concentrated under vacuum, diluted in ether, washed with brine, dried over sodium sulfate, filtered, concentrated under vacuum to yield compound 174 (1.156 g, 91%) as yellow solid.

Provenance & Evidence