3'-(Trifluoromethyl)acetophenone → (E)-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]-2-buten-1-one

HRID 231507

Reaction equation

HRID 231507 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:3].CO[C:16](OC)([N:18]([CH3:20])[CH3:19])[CH3:17]>>[CH3:19][N:18]([CH3:20])[C:16]([CH3:17])=[CH:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 676823'-(Trifluoromethyl)acetophenoneHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 53396592(E)-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]-2-buten-1-one

Procedure

A mixture of 20.0 g of 3-trifluoromethylacetophenone and 20 ml of N,N-dimethylacetamide dimethyl acetal was stirred and heated at reflux for 3 hours. The mixture was evaporated in vacuo to give a red solid. The solid was triturated with n-hexane and filtered. The solid was washed with n-hexane and dried to give 18.0 g of 3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]-2-buten-1-one as red crystals, mp 71°-73° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customThe mixture was evaporated in vacuo
  4. customto give a red solid
  5. customThe solid was triturated with n-hexane
  6. filtrationfiltered
  7. washThe solid was washed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-3cb7a6da37ae47bdaaedf2742a85337d
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Linked notes

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