2-(Dimethylamino)ethanol → HCID 53913192, compound

HRID 1382636Notes

Reaction equation

[Na].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][OH:6].[C:8]1([C:14]([C:31]([F:34])([F:33])[F:32])=[C:15]([C:24]2[CH:29]=[CH:28][C:27](F)=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][O:6][C:27]1[CH:28]=[CH:29][C:24]([C:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:31]([F:32])([F:33])[F:34])=[CH:25][CH:26]=1

Participants

Reactant 3

HCID 79022-(Dimethylamino)ethanol

HCID 5360545Sodium

HCID 53717982HCID 53717982, compound

Product 1

HCID 53913192HCID 53913192, compoundYield 89.6%

Procedure

0.46 g (0.02 g.-atoms) of sodium are dissolved in 4.5 g (50 mmoles) of 2-dimethylamino-ethanol. 3.72 g (10 mmoles) of 2-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-1-(4-methoxyphenyl)-propene are added to the solution, the mixture is heated at 150°-155° C. for one hour, and then processed as described in Example 19. 3.95 g (89.6%) of 1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-3,3,3-trifluoro-1-(4-methoxyphenyl)propene are obtained as a resinous substance; the product is a 9:1 mixture of the (Z) and (E) isomers.

Workup

temperaturethe mixture is heated at 150°-155° C. for one hour

Sources & evidence

ORD record: ord-167fb69698ca40f08af9178613835ede
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04806685

Reaction notes

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