Dimethyl Sulfoxide → Methyl 5-formyl-3-phenylthiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

DMSO (0.643 ml, 9.06 mmol) in 4 mL of DCM at −70° C. was added dropwise to a solution of oxalyl chloride (0.529 ml, 6.04 mmol) in 10 mL of DCM at −78° C. and stirred for 10 min. Then 169 (0.75 g, 3.02 mmol) in 4 mL of DCM and TEA in 4 ml, DCM were added dropwise, stirred for an additional 10 min and warmed up slowly to 0° C. The reaction mixture was poured into an ice-cooled solution of NaHCO3 (ss) and extract the product with DCM, washed with brine, dried over sodium sulfate, filtered, concentrated under vacuum to yield compound 172 (706 mg, 95%) as a beige solid.

Provenance & Evidence