Water → HCID 53920513, compound

HRID 1886489Notes

Reaction equation

HRID 1886489 reaction equation
[CH3:1][C@H:2]1[CH2:6][C:5](=[O:7])[CH2:4][C@H:3]1[C:8]([O:10]C)=[O:9].[I-].[Na+].C[Si](C)(C)Cl.O>C(#N)C>[CH3:1][C@H:2]1[CH2:6][C:5](=[O:7])[CH2:4][C@H:3]1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 22846154HCID 22846154, compound

Product 1

HCID 53920513HCID 53920513, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (5 ml) were dissolved methyl cis-2-methyl-4-oxocyclopentanecarboxylate [K. Kojima et al., Chem. Pharm. Bull., 33, 2750 (1985)] (827 mg) and sodium iodide (3.175 g), and trimethylchlorosilane (2.69 ml) was added to the solution at room temperature. The mixture was refluxed under nitrogen atmosphere for one day. After the temperature was cooled to room temperature, water was added and the mixture was extracted with ether, followed by washing with an aqueous solution of sodium thiosulfate. The water layer was further extracted with ether. The organic layers were combined, dried over magnesium sulfate and concentrated to dryness. The residue was subjected to silica gel column chromatography with ethyl acetate:chloroform (1:1), and the eluted fractions were combined and concentrated to dryness to yield the title compound (243 mg).

Workup

  1. additionwas added to the solution at room temperature
  2. temperatureThe mixture was refluxed under nitrogen atmosphere for one day
  3. extractionthe mixture was extracted with ether
  4. washby washing with an aqueous solution of sodium thiosulfate
  5. extractionThe water layer was further extracted with ether
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ee8f44a6739b4d739577ad59ad652c94
Source dataset
uspto-grants-1992_09
Patent number
US05151497

Reaction notes

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