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-on (J. Org. Chem., 1996, Vol. 61, p. 8687) (89.3 g) was dissolved 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 dichloromethane, 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 (41.2 g) as a pale yellow oil.

1. distillationAfter the solvent was distilled off under reduced pressure, and water
2. additionwas added to the residue
3. extractionextraction with dichloromethane
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-d8dee148afde43a39348a67e25976f38

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935824B2