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

HRID 747650Notes

Reaction equation

HRID 747650 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][C:4](Cl)=[O:5].[CH3:8][C:9]1([CH3:17])[O:16][C:14](=[O:15])[CH2:13][C:11](=[O:12])[O:10]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:8][C:9]1([CH3:17])[O:16][C:14](=[O:15])[CH:13]([C:4](=[O:5])[CH2:3][CH:2]([CH3:7])[CH3:1])[C:11](=[O:12])[O:10]1

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 66054Isovaleryl chloride

Product 1

HCID 594371732,2-Dimethyl-5-(3-methylbutanoyl)-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3-Methyl-butyryl chloride (7.40 mL, 60 mmol) was mixed at 0° C. with Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione; 8.7 g, 60 mmol), and 4-dimethylaminopyridine (DMAP, 15.1 g, 124 mmol) in DCM. The reaction mixture was allowed to reach r.t. over 1.75 hr. and completion of the reaction was verified by TLC. The reaction mixture was diluted with DCM, was washed 3× with 5% aq. solution of potassium bisulfate and brine. The organic phase was than dried with MgSO4. Crude product 9, 13.36 g) obtained after evaporation was used for next reaction without purification. 1H NMR (500 MHz, CDCl3): δ 1.02 (d, 6H), 1.74 (s, 6H), 2.21 (hp, 1H), 2.99 (d, 2H).

Workup

  1. washwas washed 3× with 5% aq. solution of potassium bisulfate and brine
  2. dry with materialthan dried with MgSO4

Sources & evidence

ORD record
ord-b95fc18814e849f29b5164b556d43c41
Source dataset
uspto-grants-2008_07
Patent number
US07396936B1

Reaction notes

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