HCID 10295973, compound → Diethyl 2-{4-[2-(2-oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzyl}malonate

HRID 896483Notes

Reaction equation

HRID 896483 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:27]=[CH:26][C:13]([CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)[C:5]2[CH:28]=[CH:29][CH:30]=[CH:31][C:4]=2[O:3]1>O1CCOCC1.[Pd]>[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:26][CH:27]=2)[C:5]2[CH:28]=[CH:29][CH:30]=[CH:31][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 10295973HCID 10295973, compound

Product 1

HCID 10159558Diethyl 2-{4-[2-(2-oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzyl}malonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Dissolve the compound obtained in Example 1 (6.7 g) in a dioxane/absolute ethanol mixture (100 ml/20 ml) and add palladium-on-carbon (0.5 g). Stir magnetically at ambient temperature under a hydrogen atmosphere for 76 hours. Remove the palladium-on-carbon by filtration and remove the mixture of solvents by evaporation under reduced pressure. Crystallise the resulting oil by trituration in isopropyl ether. Recrystallise the resulting precipitate from a 9/1 cyclohexane/toluene mixture.

Workup

  1. customRemove the palladium-on-carbon
  2. filtrationby filtration
  3. customremove
  4. additionthe mixture of solvents
  5. customby evaporation under reduced pressure
  6. customCrystallise the resulting oil by trituration in isopropyl ether
  7. customRecrystallise the resulting precipitate from a 9/1 cyclohexane/toluene mixture

Sources & evidence

ORD record
ord-6ffcc5c8c2554855b473af381ae846df
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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