2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 23004045, compound

HRID 322195Notes

Reaction equation

HRID 322195 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20])=[N+:12]=[N-:13]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:20])=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 14580383HCID 14580383, compound

Product 1

HCID 23004045HCID 23004045, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%).

Workup

  1. waitat room temperature for 1 hr
  2. washThe solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-60425537d9854f0c8e2429c1e77528b6
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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