Ethyl Acetate → 5,5-Dimethyl-3-naphthylcarbonyl-1,3-oxazolidine-2,4-dione

HRID 896583Notes

Reaction equation

HRID 896583 reaction equation
[K].[CH3:2][C:3]1([CH3:10])[O:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[C:11]1([C:21](Cl)=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>O1CCCC1>[CH3:2][C:3]1([CH3:10])[O:7][C:6](=[O:8])[N:5]([C:21]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:22])[C:4]1=[O:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 701461-Naphthalenecarbonyl chlorideHCID 697330845,5-Dimethyl-2,4-oxazolidinedione potassium salt

Product 1

HCID 697329845,5-Dimethyl-3-naphthylcarbonyl-1,3-oxazolidine-2,4-dioneYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,5-Dimethyl-2,4-oxazolidinedione potassium salt (84 mg) was suspended in tetrahydrofuran (1 mL), 1-naphthoyl chloride (95 mg) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added 4 mL of ethyl acetate, and the solution was filtered with a membrane filter (0.25 μm). The resulting organic layer was purified by silica gel chromatography (hexane:ethyl acetate=2:1), and further recrystallized from ethyl acetate/IPE to obtain 61 mg of white crystals.

Workup

  1. filtrationthe solution was filtered with a membrane
  2. filtrationfilter (0.25 μm)
  3. customThe resulting organic layer was purified by silica gel chromatography (hexane:ethyl acetate=2:1)
  4. customfurther recrystallized from ethyl acetate/IPE

Sources & evidence

ORD record
ord-c7913fa326e04d8abf3163c7d9726602
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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