Sodium Iodide → HCID 12040392, compound

HRID 991266Notes

Reaction equation

HRID 991266 reaction equation
[I-:1].[Na+].[CH3:3][C:4]1([CH3:13])[O:9][C:8](=[O:10])[CH:7]=[C:6]([CH2:11]Cl)[O:5]1>CC(C)=O>[I:1][CH2:11][C:6]1[O:5][C:4]([CH3:13])([CH3:3])[O:9][C:8](=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 98129102,2-dimethyl-6-chloromethyl-1,3-dioxin-4-one

Product 1

HCID 12040392HCID 12040392, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Sodium iodide (2.16 g) was dissolved in 16 mL of acetone, 2.00 g of 2,2-dimethyl-6-chloromethyl-1,3-dioxin-4-one diluted with 4 mL of acetone was added, and the mixture was stirred at room temperature for 2 hours. The insoluble matter was removed from the reaction mixture by filtration and the filtrate was concentrated. The residue was dissolved in 20 mL of chloroform, the insoluble matter was again filtered off and the filtrate was concentrated. The thus-obtained residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=1/1 (volume ratio)) to give 2.65 g of 6-iodomethyl-2,2-dimethyl-4H-1,3-dioxin-4-one as a yellow liquid. The NMR spectrum of this compound is shown below.

Workup

  1. additionwas added
  2. customThe insoluble matter was removed from the reaction mixture by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in 20 mL of chloroform
  5. filtrationthe insoluble matter was again filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe thus-obtained residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=1/1 (volume ratio))

Sources & evidence

ORD record
ord-18154c74992f4e86b1454a148ce688a9
Source dataset
uspto-grants-2002_10
Patent number
US06462223B2

Reaction notes

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