Ethanol → HCID 57481682, compound

HRID 2104359Notes

Reaction equation

HRID 2104359 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]>>[CH2:13]([O:15][C:6]([C@@H:5]1[CH2:4][CH2:3][C@H:2]2[C@H:8]([O:7]2)[CH2:9]1)=[O:10])[CH3:14]

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., vol. 61, p. 8687 (1996)) (14.3 g) was dissolved in ethanol (130 mL), and 2N aqueous sodium hydroxide (34.5 mL) was added to the solution under ice cooling, followed by stirring at room temperature for 7 hours. The solvent was distilled away under reduced pressure, and water was added to the residue. The mixture was extracted with methylene chloride, and the extract was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=83:17), to thereby give the title compound (6.54 g).

Workup

  1. distillationThe solvent was distilled away under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialthe extract was dried over sodium sulfate anhydrate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=83:17)

Sources & evidence

ORD record
ord-76f60a3631dd464187a6ad2f884b0e87
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

Loading…