4,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazole → 4-(4,4-Dimethyl-1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one

HRID 251438Notes

Reaction equation

HRID 251438 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:20][C:18]1([CH3:21])[CH2:17][O:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:19]1

Participants

5

Reactant 2

HCID 149891694,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 1357785094-(4,4-Dimethyl-1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-oneYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-benzyloxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole ax4 (4.0 g, 140 mmol, 1 eq) in ethanol (200 ml) is added 1.5 g of 10% Pd/C (1.42 mmol, 0.1 eq). The mixture is stirred for 48 h at room temperature, under 40 psi of a hydrogen atmosphere. The mixture is then filtered on celite and the solvent removed under vacuum. The residual solid is triturated in hexane to give 2.6 g of 4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenol ax7.

Workup

  1. filtrationThe mixture is then filtered on celite
  2. customthe solvent removed under vacuum
  3. customThe residual solid is triturated in hexane

Sources & evidence

ORD record
ord-1024aa6b23ec465b9c50920e9cba2584
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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