Ethanol → 5-[6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-oxazolidinedione

HRID 1050

Reaction equation

HRID 1050 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:25]=[CH:24][C:18]2[CH:19]=[C:20]([CH:22]=O)[O:21][C:17]=2[CH:16]=1.[O:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].N1CCCC1.C(O)C>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:25]=[CH:24][C:18]2[CH:19]=[C:20]([CH2:22][CH:30]3[O:26][C:27](=[O:32])[NH:28][C:29]3=[O:31])[O:21][C:17]=2[CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 31268PyrrolidineHCID 973892,4-OxazolidinedioneHCID 196943726-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde

Product 1

HCID 702831595-[6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-oxazolidinedioneYield 6.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde (1.70 g), 2,4-oxazolidinedione (1.55 g), pyrrolidine (0.365 g) and ethanol (40 ml) was heated under refluxing conditions for 3 hours. The reaction mixture was poured over water; the resulting crystals were collected by filtration. The crystals were dissolved in tetrahydrofuran (100 ml); after palladium-carbon (0.40 g) was added, the mixture was subjected to catalytic reduction at room temperature under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with methanolchloroform (2:98, v/v), crystals of 5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-oxazolidinedione (0.14 g, 6.6%) were obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 172° to 173° C.

Workup

  1. temperaturewas heated under refluxing conditions for 3 hours
  2. filtrationthe resulting crystals were collected by filtration
  3. dissolutionThe crystals were dissolved in tetrahydrofuran (100 ml)
  4. additionafter palladium-carbon (0.40 g) was added
  5. customwas subjected to catalytic reduction at room temperature under an atmospheric pressure of 1 atm
  6. filtrationAfter the catalyst was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washFrom the fraction eluted with methanolchloroform (2:98

Sources & evidence

ORD record
ord-76206d3ad92c4c3493b9dddaa1158ad8
Source dataset
uspto-grants-1998_03
Patent number
US05723479

Linked notes

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