2-Phenylacetophenone → 1,2,3-triphenylpropan-1-one

HRID 566513Notes

Reaction equation

HRID 566513 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+]>CN(C=O)C.C(Br)C1C=CC=CC=1>[C:1]1([C:7](=[O:8])[CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 99482-PhenylacetophenoneHCID 24758Sodium hydride

Product 1

HCID 2334321,2,3-triphenylpropan-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7498Benzyl BromideSolvent

Procedure

To deoxybenzoin (0.20 g, 1.02 mmol) in DMF (5 mL) were added at 0° C. NaH in oil (0.050 g, 1.22 mmol) and benzyl bromide (183 μL). After 1 h at room temperature, the reaction mixture was partitioned between NH4OAc and ether. After usual work up procedure the title compound was purified by flash chromatography (0.95 g).

Workup

  1. customthe reaction mixture was partitioned between NH4OAc and ether
  2. customAfter usual work up procedure the title compound was purified by flash chromatography (0.95 g)

Sources & evidence

ORD record
ord-3ad1d3486b6648579074d670d1e39c51
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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