Dicyclohexylcarbodiimide → 4-(2'-Chloro-4-biphenylyl)-2-butanone

HRID 1605655Notes

Reaction equation

HRID 1605655 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]([OH:18])[CH3:17])=[CH:10][CH:9]=1.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 9813011pyridine TFAHCID 215471324-(2'-Chloro-4-biphenylyl)-2-butanol

Product 1

HCID 215261804-(2'-Chloro-4-biphenylyl)-2-butanoneYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-(2'-Chloro-4-biphenylyl)-2-butanone was prepared analogous to Example 42 from 4-(2'-chloro-4-biphenylyl)-2-butanol by oxidation with dimethyl sulfoxide in the presence of pyridinium trifluoroacetate and N,N'-dicyclohexyl-carbodiimide with a yield of 92% of theory. The colorless crystals melted at 34°-35°C after column-chromatographic purification on silicagel, using benzene/petroleum ether (ratio by volume = 2:1) as eluant, and recrystallization from petroleum ether and ethanol.

Workup

  1. customThe colorless crystals melted at 34°-35°C after column-chromatographic purification on silicagel
  2. customrecrystallization from petroleum ether and ethanol

Sources & evidence

ORD record
ord-3a1587ae51f14166aa64d24c3038932f
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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