Acetic Acid → HCID 69830571, compound

HRID 1584300Notes

Reaction equation

HRID 1584300 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:19][CH:20]=1)[CH:7]=[CH:8][CH:9]=O)[CH3:2].[O:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].N1CCCCC1.C(O)(=O)C>O1CCCC1.[C].[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:7][CH2:8][CH2:9][CH:31]2[O:27][C:28](=[O:33])[NH:29][C:30]2=[O:32])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:19][CH:20]=1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 54112687HCID 54112687, compound

Product 1

HCID 69830571HCID 69830571, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-ethoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (3.0 g), 2,4-oxazolidinedione (1.7 g), piperidine (0.73 g) and acetic acid (50 ml) was stirred for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure, and resulting crystalline precipitate was collected by filtration. The filtrate was dissolved in ethyl acetate. The solution was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N HCl and water, followed by drying (MgSO4). The ethyl acetate layer was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), further crystals were collected, which were combined with the crystalline product obtained above and dissolved in tetrahydrofuran (THF) (100 ml). To the solution was added palladium-carbon (5%, 1.0 g), which was subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), 5-[3-[3-ethoxy-4-(2-phenyl-4-oxazolylmethoxy)phenyl]propyl]-2,4-oxazolidinedione was obtained, which was recrystallized from chloroform-ether to give colorless prisms, m.p.119-120° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customresulting crystalline precipitate
  4. filtrationwas collected by filtration
  5. dissolutionThe filtrate was dissolved in ethyl acetate
  6. washThe solution was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N HCl and water
  7. dry with materialby drying (MgSO4)
  8. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  9. washFrom the fraction eluted with chloroform-methanol (50:1), further crystals
  10. customwere collected
  11. customobtained above and
  12. customwas subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature
  13. filtrationThe catalyst was filtered off
  14. concentrationthe filtrate was concentrated
  15. washFrom the fraction eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-5c930cc0f7da4f05bd6ab045f4ca721f
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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