Ethylene Glycol → 1,4,8-Trioxaspiro[4.5]dec-6-ylacetaldehyde

Temperature

120 °C

A mixture of 3-(prop-2-en-1-yl)tetrahydro-4H-pyran-4-one (1.00 g, 7.13 mmol), ethylene glycol (0.597 mL, 10.70 mmol) and p-toluenesulfonic acid monohydrate (0.136 g, 0.713 mmol) in toluene (30 mL) was heated to 120° C. overnight. The reaction was then cooled to rt and concentrated. The residue was purified via column chromatography and used in the next step. To a mixture of 6-(prop-2-en-1-yl)-1,4,8-trioxaspiro[4.5]decane (0.840 g, 4.56 mmol) and osmium tetraoxide (2.5 wt % in T-BuOH, 0.551 mL, 0.046 mmol) in THF (15 mL) and water (5 mL) at rt was added sodium periodate (2.15 g, 1.19 mmol) portionwise over 5 min. The mixture was stirred at rt for 2 hr. The reaction was then quenched with sat'd. aq. sodium sulfite. The mixture was extracted 3× with Et2O. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 9.71 (s, 1H), 3.81-3.99 (m, 6H), 3.64-3.70 (m, 1H), 3.47 (dd, 1H, J=8.6 Hz, 11.5 Hz), 2.49-2.57 (m, 2H), 2.18-2.26 (m, 1H), 1.65-1.82 (m, 2H).

1. temperatureThe reaction was then cooled to rt
2. concentrationconcentrated
3. customThe residue was purified via column chromatography
4. customThe reaction was then quenched with sat'd
5. extractionThe mixture was extracted 3× with Et2O
6. dry with materialThe combined organics were dried (anhd. Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by column chromatography

ORD record

ord-69baf18d8b26484bb4e36d096cf9c749

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829196B2