Tributylamine → HCID 68612603, compound

HRID 1848289Notes

Reaction equation

HRID 1848289 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(N(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]([OH:25])([C:21]([F:22])([F:23])[F:24])[CH2:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)=[O:11])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 745011-(4-(Methylthio)phenyl)ethan-1-oneHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 68612603HCID 68612603, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

0.50 g (3.01 mmol) of 1-(4-(methylthio)phenyl)ethanone, 0.73 g of (3.01 mmol) of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 1.46 g of toluene and 0.17 g (0.90 mmol) of tributylamine were fed and the mixture was stirred for 15 hours at 60° C. After leaving the reaction mixture for one night at room temperature, separation operation was performed by adding 30 ml of ethyl acetate and 10 ml of water, and the ethyl acetate phase was washed with diluted aqueous solution of hydrochloric acid. After removing the solvent by distilling under reduced pressure, the residue was purified by silica gel column chromatography to obtain 0.56 g of 3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-(methylthio)phenyl)butan-1-one (yield 45.2%).

Workup

  1. customAfter leaving the reaction mixture for one night at room temperature
  2. customseparation operation
  3. additionby adding 30 ml of ethyl acetate and 10 ml of water
  4. washthe ethyl acetate phase was washed with diluted aqueous solution of hydrochloric acid
  5. customAfter removing the solvent
  6. distillationby distilling under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08b43d38544441e89e69e11f9ce68685
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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