Sodium Iodide → HCID 54155194, compound

HRID 1460728Notes

Reaction equation

HRID 1460728 reaction equation
[N+:1](=[C:3]([C:10]([CH3:12])=[O:11])[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[N-:2].[I-].[Na+].C(N(CC)CC)C.[CH3:22][Si:23](Cl)([CH3:25])[CH3:24]>C(#N)C>[N+:1](=[C:3]([C:10]([O:11][Si:23]([CH3:25])([CH3:24])[CH3:22])=[CH2:12])[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[N-:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 541706512-Diazonio-3-oxo-1-[(prop-2-en-1-yl)oxy]but-1-en-1-olate

Product 1

HCID 54155194HCID 54155194, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into 5 ml of dry acetonitrile were added 167 mg (1 millimole) of allyl 2-diazoacetoacetate and 210 mg (1.4 millimoles) of sodium iodide. To the mixture were added 220 μl (1.6 millimoles) of triethylamine and then 190 μl (1.5 millimoles) of trimethylsilyl chloride while agitating under an argon atmosphere at a room temperature. After the resultant was agitated at a room temperature for an hour, it was concentrated under a reduced pressure. To the residue was added 10 ml of dry hexane, and the resultant was agitated for 30 min. at a room temperature. Isoluble materials were removed by filtration and the hexane solution was concentrated to dryness under a reduced pressure to give 176 mg (yield 78.8%) of the desired compound in an oily state.

Workup

  1. concentrationit was concentrated under a reduced pressure
  2. additionTo the residue was added 10 ml of dry hexane
  3. stirringthe resultant was agitated for 30 min. at a room temperature
  4. customIsoluble materials were removed by filtration
  5. concentrationthe hexane solution was concentrated to dryness under a reduced pressure

Sources & evidence

ORD record
ord-7733eaacad754abcbde5ac80cf11d5cf
Source dataset
uspto-grants-1991_12
Patent number
US05071966

Reaction notes

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