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

HRID 1392737Notes

Reaction equation

HRID 1392737 reaction equation
I[C@@H:2]1[C@@H:8]2[CH2:9][C@@H:5]([C:6](=[O:10])[O:7]2)[CH2:4][CH2:3]1.[OH-].[Na+].[CH2:13]([OH:15])[CH3:14]>>[C@@H:3]12[O:15][C@@H:13]1[CH2:14][CH2:9][C@H:5]([C:6]([O:7][CH2:8][CH3:2])=[O:10])[CH2:4]2

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13487220HCID 13487220, compound

Product 1

HCID 57416186Ethyl (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylate

Procedure

(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).

Workup

  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)

Sources & evidence

ORD record
ord-b7d82b57d1c2434f91d3f3cb95021a01
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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