Triacetoxyperiodinane → HCID 71302026, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanol (7 g, 40.6 mmol) in dichloromethane (400 mL) was added Dess-Martin periodinane (43 g, 101.6 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 (2×100 mL), washed with a saturated aqueous sodium bicarbonate solution (3×200 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was diluted with n-hexane (400 mL) and filtered. The filtrate was concentrated in vacuo to afford (1,4-dioxa-spiro[4.4]non-7-yl)-acetaldehyde (5.5 g, 79%) as a light yellow solid: LC/MS m/e calcd for C9H14O3 [M+H]+ 171.21.

Provenance & Evidence