Tetrahydrofuran → 5-[(2H-1,3-Benzodioxol-5-yl)methylidene]-3-ethyl-1,3-oxazolidine-2,4-dione

HRID 1460887Notes

Reaction equation

HRID 1460887 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[CH2:12]([N:14]1[C:18](=[O:19])[CH2:17][O:16][C:15]1=[O:20])[CH3:13].C1COCC1.[H-].[Na+]>O>[CH2:12]([N:14]1[C:18](=[O:19])[C:17](=[CH:7][C:6]2[CH:1]=[CH:2][C:3]3[O:11][CH2:10][O:9][C:4]=3[CH:5]=2)[O:16][C:15]1=[O:20])[CH3:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8438PiperonalHCID 24758Sodium hydrideHCID 22323571HCID 22323571, compound

Product 1

HCID 537634375-[(2H-1,3-Benzodioxol-5-yl)methylidene]-3-ethyl-1,3-oxazolidine-2,4-dioneYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.16 g (7.73 mmol) of piperonal and 1.00 g (7.75 mmol) of N-ethyl-2,4-oxazolidinedione are introduced into a 50 ml of eggplant-shaped flask, and a spiral condenser and a drying tube are mounted thereon. The reaction vessel is internally charged with an atmosphere of nitrogen and about 10 ml of THF dried with molecular sieve is added, followed by dissolution by stirring with a magnetic stirrer. After dissolution, 0.36 g (9.0 mmol) of NaH (60 wt. %, oily) is added little by little under stirring with magnetic stirrer. After stirring at room temperature for 2 hours, the reaction mixture is poured into water. The oily substance formed is extracted with ethyl acetate, and after drying over magnesium sulfate, the solvent is removed under reduced pressure, followed by recrystallization from methanol to give 0.34 g (1.3 mmol) of N-ethyl-5-(3,4-methylenedioxy-benzylidene)-2,4-oxazolidinedione at a yield of 17 % (m.p.=135°-137 ° C.).

Workup

  1. customdried with molecular sieve
  2. additionis added
  3. dissolutionfollowed by dissolution
  4. additionis added little by little
  5. stirringunder stirring with magnetic stirrer
  6. stirringAfter stirring at room temperature for 2 hours
  7. customThe oily substance formed
  8. extractionis extracted with ethyl acetate
  9. dry with materialafter drying over magnesium sulfate
  10. customthe solvent is removed under reduced pressure
  11. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-ffccd30796f94bbd904fe1261a62e9c2
Source dataset
uspto-grants-1991_12
Patent number
US05072451

Reaction notes

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