Triacetoxyperiodinane → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-(5-formyl-2-thienyl)acetate

Participants

Reaction Steps

To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-(hydroxymethyl)-2-thienyl]acetate (100 mg, 0.20 mmol) in dichloromethane (2 mL) was added Dess-Martin periodinane (102 mg, 0.24 mmol) at −78° C. The reaction was stirred at room temperature for 30 min. The reaction solution was washed with saturated aqueous Na2S2O3 (5 mL) and saturated aqueous sodium bicarbonate (5 mL). The organic phase was passed through a hydrophobic fit and concentrated in vacuo to give the title compound as a pale yellow oil (100 mg, quantitative yield) which was used in the next step without further purification.

Provenance & Evidence