Ethanol → HCID 57481682, compound

HRID 546452Notes

Reaction equation

HRID 546452 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]>>[O:15]1[C@@H:2]2[C@H:13]1[CH2:14][C@H:5]([C:6]([O:7][CH2:8][CH3:9])=[O:10])[CH2:4][CH2:3]2

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 1140249819914-92-2

Product 1

HCID 57481682HCID 57481682, compound

Procedure

(1R*,4R*,5R*)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 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 sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil.

Workup

  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 sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)

Sources & evidence

ORD record
ord-2d2aaf187db64d32bf72ffe17dd807ce
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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