Tetramethylammonium fluoride → 5-[2-(2-Chloro-5-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

HRID 1096008Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:21])[C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12].[F:22][C:23]([Si](C)(C)C)([F:25])[F:24].[F-].C[N+](C)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:21])[C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)([OH:12])[C:23]([F:25])([F:24])[F:22]

Participants

Reactant 3

HCID 67803Tetramethylammonium fluoride

HCID 552549(Trifluoromethyl)trimethylsilane

HCID 666992895-[2-(2-Chloro-5-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 574213245-[2-(2-Chloro-5-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

Procedure

In analogy to Example 165, step 3, 5-[2-(2-chloro-5-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one was reacted with (trifluoromethyl)trimethylsilane and tetramethylammonium fluoride to give the title compound as a light grey foam. MS (m/e)=376.2 [M+H+].

Sources & evidence

ORD record: ord-cbbe6c291da14c8aa81c68ec9cd8aa25
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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