2-(Dimethylamino)ethanol → HCID 53792218, compound

HRID 1382634Notes

Reaction equation

HRID 1382634 reaction equation
[Na].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][OH:6].[C:8]1([C:14]([C:28]2[CH:33]=[CH:32][C:31](F)=[CH:30][CH:29]=2)=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][O:6][C:31]1[CH:30]=[CH:29][C:28]([C:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:15]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:16]([F:19])([F:18])[F:17])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 5360545SodiumHCID 54385624HCID 54385624, compound

Product 1

HCID 53792218HCID 53792218, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.39 g (0,017 g.-atoms) of sodium are dissolved in 3.12 g (35 mmoles) of 2-dimethylamino-ethanol. 3.15 g (8.5 mmoles) of 1-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-2-(4-methoxyphenyl)-propene are added to the solution, and the mixture is heated at 150°-155° C. for one hour. The reaction mixture is cooled, diluted with 200 ml of ether, washed with water until neutral, dried and evaporated. The residue is dissolved in 30 ml of hexane, the solution is filtered, and the filtrate is evaporated. 3.39 g (90%) of 1-[4-(2-dimethylamino-ethoxy)-phenyl]-1-phenyl-3,3,3-trifluoro-2-(4-methoxyphenyl)-propene are obtained as a resinous substance; the product is a 3:4 mixture of the (Z) and (E) isomers.

Workup

  1. temperaturethe mixture is heated at 150°-155° C. for one hour
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water until neutral,
  4. customdried
  5. customevaporated
  6. dissolutionThe residue is dissolved in 30 ml of hexane
  7. filtrationthe solution is filtered
  8. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-972c2832664e4df1b7dcb20acfd7059f
Source dataset
uspto-grants-1989_02
Patent number
US04806685

Reaction notes

Loading…