2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 546882Notes

Reaction equation

HRID 546882 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[Br:11][C:12]1[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][CH:17]=1>C(OC(=O)C)(=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15](=[C:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])[NH:14][CH:13]=1

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 142763Pyridine, 3-bromo-, 1-oxide

Product 1

HCID 574434985-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 33%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Meldrum's acid (6.63 g, 45.98 mmol) was added to a solution of 3-bromopyridine N-oxide (8 g, 45.98 mmol) in acetic anhydride (50 mL), and the mixture was stirred at room temperature overnight. Then, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate and ethyl acetate) to give the target compound (4.53 g, 33%).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate and ethyl acetate)

Sources & evidence

ORD record
ord-8508f2ddddb94deb899cc4ae3deafdac
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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