2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 58110062, compound

HRID 1803219Notes

Reaction equation

HRID 1803219 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[C:11]1([C:17]2([CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26])[O:21][CH2:20][CH2:19][O:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]([C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:17]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:18][CH2:19][CH2:20][O:21]2)[C:4](=[O:9])[O:3]1

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 86649924HCID 86649924, compound

Product 1

HCID 58110062HCID 58110062, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Step AAH (3): To a soln of 2,2-dimethyl-1,3-dioxane-4,6-dione (329 mg, 2.281 mmol) in dichloromethane (10 mL) was added DMAP (405 mg, 3.32 mmol). After stirring for 10 min, a solution of 4-(2-phenyl-1,3-dioxolan-2-yl)butanoyl chloride (2.07 mmol) in dichloromethane was added at 0° C. under nitrogen. The mixture was stirred at rt for 3 his. The crude reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc. The organic layer was sequentially washed with 1.0 N aqueous HCl, 1.0 N aqueous NaOH, and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to 2,2-dimethyl-5-(4-(2-phenyl-1,3-dioxolan-2-yl)butanoyl)-1,3-dioxane-4,6-dione (700 mg, 1.93 mmol, 93% yield).

Workup

  1. stirringThe mixture was stirred at rt for 3 his
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washThe organic layer was sequentially washed with 1.0 N aqueous HCl, 1.0 N aqueous NaOH, and water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ab8ce1b6cb0f4a75a5c980b7cd01ab74
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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