Sodium Iodide → HCID 12034529, compound

HRID 546717Notes

Reaction equation

HRID 546717 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[I-].[Na+].[OH:14][CH:15]([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH2:16][C:17]([O:19][CH3:20])=[O:18]>C(#N)C>[CH3:25][C:24]1([CH3:26])[O:14][CH:15]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 34560336-Octenoic acid, 3-hydroxy-7-methyl-, methyl esterHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 12034529HCID 12034529, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cerium chloride heptahydrate (812 mg) and sodium iodide (327 mg) were added to a solution of methyl 3-hydroxy-7-methyl-6-octenoate obtained by the method described in Heterocycles, 34, 1107-1117 (1992) (4.06 g) in acetonitrile (10 ml), and the reaction solution was heated under reflux for 10 hours. The reaction solution was left to cool and then concentrated under reduced pressure. Diethyl ether and 12 ml of 1 N hydrochloric acid were added to the resulting residue, and the organic layer was separated. Diethyl ether was added to the aqueous layer, and the organic layer was separated. The combined organic layers were sequentially washed with water, a saturated sodium bicarbonate solution (pH=9), a 5% sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 2.65 g of the title compound. The property values of the compound are as follows.

Workup

  1. customobtained by the method
  2. temperatureunder reflux for 10 hours
  3. waitThe reaction solution was left
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure
  6. additionDiethyl ether and 12 ml of 1 N hydrochloric acid were added to the resulting residue
  7. customthe organic layer was separated
  8. additionDiethyl ether was added to the aqueous layer
  9. customthe organic layer was separated
  10. washThe combined organic layers were sequentially washed with water
  11. dry with materiala saturated sodium bicarbonate solution (pH=9), a 5% sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-c784d869438844fcba4bdb96decd4dc4
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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