Triacetoxyperiodinane → HCID 67229036, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanol (2.5 g, 5.84 mmol) in dichloromethane (150 mL) was added Dess-Martin periodinane (6.2 g, 14.6 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 2 h and then quenched with a saturated aqueous sodium bicarbonate solution (100 mL). The mixture was extracted with dichloromethane (50 mL), washed with a saturated aqueous sodium bicarbonate solution (3×100 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 50% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanone (2.45 g, 98%) as a light yellow solid: LC/MS m/e calcd for C22H22N2O5S [M+H]+ 427.50, observed 427.5.

Provenance & Evidence