Phenylacetone → (Z)-4-(3-Benzyloxy-4-nitrophenyl)-3-phenyl-but-3-en-2-one

HRID 660487Notes

Reaction equation

HRID 660487 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([CH2:26][C:27](=[O:29])[CH3:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[C:26](/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)\[C:27](=[O:29])[CH3:28])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 8082PiperidineHCID 12111719HCID 12111719, compound

Product 1

HCID 68842235(Z)-4-(3-Benzyloxy-4-nitrophenyl)-3-phenyl-but-3-en-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 3-benzyloxy-4-nitrobenzaldehyde (83, step A) (1.16 g, 4.5 mmol) and 1-phenylpropane-2-one (0.726 g, 5.4 mmol) in toluene (50 mL) is added a catalytic amount of piperidine/glacial acetic acid and the mixture is refluxed for 3 h using a Dean-Stark apparatus. The mixture is cooled to room temperature and concentrated under reduced pressure. The crude material is purified by flash chromatography using a gradient of 15-50% EtOAc/hexane as eluent to give the title compound as an oil.

Workup

  1. temperaturethe mixture is refluxed for 3 h
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-d23ebc5137754c08aaf0750f191a3cd9
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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