Pyridine → HCID 23004129, compound

HRID 322191Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.N1C=CC=CC=1.[N:17]([CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24])=[N+:18]=[N-:19]>C(Cl)Cl>[N:17]([CH2:20][CH2:21][CH2:22][C:23]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:24])=[N+:18]=[N-:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (3.82 g, 26.5 mmol) and pyridine (4.20 g, 53.0 mmol) in 150 ml of CH2Cl2 was added dropwise a solution of crude 4-azidobutyric chloride (3.90 g, 26.5 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 (60 ml), water (60 ml) followed by brine (60 ml) and dried. After evaporation of solvent, 5-(4-azidobutanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light pink oil (6.20 g, 92%).

Workup

waitat room temperature for 1 hr
washThe solution was washed with 0.5N aqueous HCl (60 ml), water (60 ml)
customdried
customAfter evaporation of solvent

Sources & evidence

ORD record: ord-c5e8b8fbaa184642aab2d72f4671ec7d
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211198B1

Reaction notes

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