2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 23004044, compound

HRID 322203Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[CH3:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (5.77 g, 40.0 mmol) and 4-dimethylaminopyridine (5.86 g, 44.0 mmol) in 100 ml of CH2Cl2 was added dropwise the solution of crude 5-methoxyvaleric chloride (6.00 g, 39.9 mmol) in 10 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for an additional 1 hr. The solution was washed with 1N aqueous HCl (100 ml) and brine (250 ml). After dried over Na2SO4 and evaporation of solvent, 5-(5-methoxypentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light pink oil (9.20 g, 89%).

Workup

waitat room temperature for an additional 1 hr
washThe solution was washed with 1N aqueous HCl (100 ml) and brine (250 ml)
dry with materialAfter dried over Na2SO4 and evaporation of solvent

Sources & evidence

ORD record: ord-de1133130f6843aebf9f1ac0a4865af7
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211198B1

Reaction notes

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