2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 86665308, compound

HRID 403009Notes

Reaction equation

HRID 403009 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[I:11]C1(OC(=O)C)COC(=O)N1OC(=O)C>ClCCl>[IH2+:11].[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 66734184HCID 66734184, compound

Product 1

HCID 86665308HCID 86665308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-dimethyl-4,6-dioxo-1,3-dioxane (0.30 mmol) was added under argon to a solution of the iododiacetoxy oxazolidinone analog 25 (0.30 mmol) in anhydrous dichloromethane (6 mL) and the solution was stirred at room temperature overnight. The solvent was then evaporated and the product purified by flash chromatography on silica gel using 60-70% ethyl acetate in hexane as eluent to give the iodonium ylide 2,2-Dimethyl-4,6-dioxo-1,3-dioxane iodonium ylide derivative 26 as a white solid in 16% yield.

Workup

  1. customThe solvent was then evaporated
  2. customthe product purified by flash chromatography on silica gel using 60-70% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-51eecc7d59924cdd867db2be84eb8bae
Source dataset
uspto-grants-2014_06
Patent number
US08742139B2

Reaction notes

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