Ethanol → Ethyl (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylate

(1S,4S,5S)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (89.3 g) was suspended in ethanol (810 ml), a 2N aqueous solution (213 ml) of sodium hydroxide was added, and the mixture was then stirred at room temperature for 3 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with methylene chloride, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=17:3) to obtain the title compound (41.3 g).

1. distillationAfter the solvent was distilled off under reduced pressure, and water
2. additionwas added to the residue
3. extractionextraction with methylene chloride
4. dry with materialthe extract was dried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=17:3)

ORD record

ord-ccfb331ec9054e3a8262a518248c42c5

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365205B2