Tetrahydrofuran → (3aR,6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one

Temperature

0 °C

Enantiomerically pure (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (bis-THF) 27 (85 mg, 0.65 mmol) was diluted in dry CH2Cl2 (6 mL) under argon, the solution was cooled to 0° C. and anhydrous Na2HPO4 (52 mg, 0.36 mol) was added. Dess-Martin periodinane (360 mg, 0.85 mmol) was added at once at 0° C. and the resulting suspension warmed to 23° C. and stirred for 3 h. The reaction was then quenched by successive addition of sat. aq. NaHCO3 and sat. aq. Na2SO3 solutions (1.5+1.5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 then EtOAc. The combined organic phases were dried (Na2SO4), filtered on a small pad of silica gel, and evaporated to dryness. The residue was purified by column chromatography on silica gel using hexanes/EtOAc (3:1) to furnish ketone 28 (73 mg, 87%) as a white crystalline solid. TLC: Rf=0.57 (hexanes/EtOAc=1:1); Spectral data corresponded to those previously reported in the literature.35

1. temperaturethe resulting suspension warmed to 23° C.
2. customThe reaction was then quenched by successive addition of sat. aq. NaHCO3 and sat. aq. Na2SO3 solutions (1.5+1.5 mL)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with CH2Cl2
5. dry with materialThe combined organic phases were dried (Na2SO4)
6. filtrationfiltered on a small pad of silica gel
7. customevaporated to dryness
8. customThe residue was purified by column chromatography on silica gel

ORD record

ord-368d59a09d1642a09c9dffe93d22acf5

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024038B2