Water → 2-(4-Benzyloxyphenylmethylene)-4-methyl-3-oxopentanamide

HRID 277567

Reaction equation

HRID 277567 reaction equation
[CH3:1][CH:2]([CH3:15])[C:3](=[O:14])[CH2:4][C:5]([NH:7]C1C=CC=CC=1)=[O:6].[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1.O>C1(C)C(C)=CC=CC=1>[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[C:4]([C:3](=[O:14])[CH:2]([CH3:15])[CH3:1])[C:5]([NH2:7])=[O:6])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 102198994-methyl-3-oxo-N-phenylpentanamide

Product 1

HCID 540483912-(4-Benzyloxyphenylmethylene)-4-methyl-3-oxopentanamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Step A—A solution of 4-methyl-N-phenyl-3-oxopentanamide, 12, (5 mmol), 4-benzyloxybenzaldehyde (5 mmol) and pyridine (1 mL) in xylene (100 mL) is heated at reflux, with azeotropic removal of water. The progress of the reaction is monitored by tlc. When the reaction is complete, the solvent is removed under reduced pressure, and the residue is chromatographed to afford 2-(4-benzyloxyphenylmethylene)-4-methyl-3-oxopentanamide, 13, (R=4-benzyloxy).

Workup

  1. customthe solvent is removed under reduced pressure
  2. customthe residue is chromatographed

Sources & evidence

ORD record
ord-dd175ec9fb224853972661988935f5aa
Source dataset
uspto-grants-2002_03
Patent number
US06355810B1

Linked notes

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