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2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(5-Azidopentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 396682
Notes
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Reaction equation

HRID 396682 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][C:18](Cl)=[O:19])=[N+:12]=[N-:13]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:19])=[N+:12]=[N-:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 109317475-azidopentanoyl Chloride

Product 1

HCID 230040735-(5-Azidopentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To the solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (4.45 g, 30.9 mmol) and 4-dimethylaminopyridine (7.55 g, 61.8 mmol) in 100 ml of CH2Cl2 was added the solution of crude 5-azidovaleric chloride in 10 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr and at room temperature for 1 hr. The solution was washed with 1N aqueous HCl (100 ml), brine (250 ml) and dried over Na2SO4. After evaporation of solvent, 5-(5-azidopentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light pink oil (8.17 g, 98%).

Workup

  1. washThe solution was washed with 1N aqueous HCl (100 ml), brine (250 ml)
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-36dd19fa668e420fa2669556bab451ab
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06608086B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes