Triacetoxyperiodinane → HCID 71302026, compound

Temperature

25 °C

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.

1. customquenched with a saturated aqueous sodium bicarbonate solution (100 mL)
2. extractionThe mixture was extracted with dichloromethane (2×100 mL)
3. washwashed with a saturated aqueous sodium bicarbonate solution (3×200 mL), brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. additionThe residue was diluted with n-hexane (400 mL)
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-c9b7b2e0de4b4d51a88231fb911fcf43

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222416B2