Sodium Iodide → HCID 585393, compound

HRID 1699987Notes

Reaction equation

HRID 1699987 reaction equation
[I-].[Na+].C[Si](C)(C)Cl.[C:8]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11].[CH:17]1[C:22]([CH:23]=O)=[CH:21][C:20]2[O:25][CH2:26][O:27][C:19]=2[CH:18]=1>C(#N)C.CCOCC.O>[CH2:15]([O:14][C:8](=[O:13])[CH:9]([CH2:23][C:22]1[CH:17]=[CH:18][C:19]2[O:27][CH2:26][O:25][C:20]=2[CH:21]=1)[C:10](=[O:11])[CH3:12])[CH3:16]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8438PiperonalHCID 8868Ethyl Acetoacetate

Product 1

HCID 585393HCID 585393, compoundYield 32.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of 117.2 g sodium iodide in 700 ml of acetonitrile, first 85.9 g trimethylchlorosilane and then 20.56 g ethyl acetoacetate were dropped in at room temperature. After cooling down to 0-5° C., a solution of 23.65 g Piperonal in 50 ml of acetonitrile was dropped in. Then the mixture was stirred at room temperature for 5 hours and then at 60° C. overnight. After the mixture was cooled down to room temperature it was diluted with ether and water. The organic phase was separated and washed with saturated sodium thiosulfate until the color of the iodine was gone. Then the organic phase was washed with water, dried, filtered and evaporated to dryness. The resulting dark oil was purified by chromatography to yield 13.7 g of a yellow oil.

Workup

  1. customat 60° C.
  2. customovernight
  3. temperatureAfter the mixture was cooled down to room temperature it
  4. customThe organic phase was separated
  5. washwashed with saturated sodium thiosulfate until the color of the iodine
  6. washThen the organic phase was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe resulting dark oil was purified by chromatography

Sources & evidence

ORD record
ord-770e9b7eecaf49b9a5139f200a258d9a
Source dataset
uspto-grants-2002_02
Patent number
US06348618B1

Reaction notes

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