Ethyl Acetate → HCID 10320206, compound

HRID 257624Notes

Reaction equation

HRID 257624 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:26](=C)C(OCC)=O)[CH:23]=[CH:24][CH:25]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33]([O:36][CH2:37][CH3:38])(=[O:35])[CH3:34]>[Pd]>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH2:26][CH2:34][C:33]([O:36][CH2:37][CH3:38])=[O:35])[CH:23]=[CH:24][CH:25]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 67854984HCID 67854984, compound

Product 1

HCID 10320206HCID 10320206, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of ethyl 3-[2-(4,5-diphenyl-2oxazolyl)-ethyl]phenyl-2-propenoate (1.02 g, 2.4 mmol) in ethyl acetate (50 mL) was hydrogenated over 10% palladium on charcoal (0.06 g) at 35 psi. After 27 hours, the mixture was filtered, concentrated and the residue subjected to chromatography on a column of silica gel using a mixture of ethyl acetate and hexanes (9:1) as eluent. Elution gave ethyl 3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]benzene propanoate (0.92 g, 90%) as an oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. additiona mixture of ethyl acetate and hexanes (9:1) as eluent
  4. washElution

Sources & evidence

ORD record
ord-2a0db456a80042509a03ceacdadabbf8
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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