(Trifluoromethyl)trimethylsilane → 1,1,1-Trifluoro-2-(2-methyl-pyridin-4-yl)-3-phenyl-butan-2-ol

HRID 1097861Notes

Reaction equation

HRID 1097861 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[CH3:9][C:10]1[CH:15]=[C:14]([C:16](=[O:25])[CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH:13]=[CH:12][N:11]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:1][C:2]([F:4])([F:3])[C:16]([C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:9])[CH:15]=1)([OH:25])[CH:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:18]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilane2×HCID 11726816Tetrabutylammonium Fluoride Trihydrate2×HCID 574213311-(2-Methyl-pyridin-4-yl)-2-phenyl-propan-1-one

Product 1

HCID 252527581,1,1-Trifluoro-2-(2-methyl-pyridin-4-yl)-3-phenyl-butan-2-olYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoromethyltrimethylsilane (2N in THF, 0.76 mL, 1.5 mmol) was added at 0° C. to a solution of 1-(2-methyl-pyridin-4-yl)-2-phenyl-propan-1-one (142 mg, 0.63 mmol) in THF (5 mL), followed by the addition of tetrabutylammonium fluoride trihydrate (40 mg, 0.13 mmol). After stirring overnight at r.t., an additional amount of trifluoromethyl-trimethylsilane (0.38 mL), followed by tetrabutylammonium fluoride trihydrate (20 mg) was added to drive the reaction towards completion. The solvent was evaporated, the residue was taken up in methanol, and the title compound (42 mg, 23%) was isolated by reversed-phase, preparative HPLC (Agilent Zorbax XdB-C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA[aq]). 1H NMR (300 MHz, DMSO-D6) □ 8.25 (1H, d), 7.17 (1H, s), 7.11 (2H, d), 7.09-7.00 (4H, m), 6.93 (1H, s), 3.62 (1H, q), 2.35 (3H, s), 1.42 (3H, d); MS (m/e)=296.4 [MH+].

Workup

  1. additionwas added
  2. customthe reaction towards completion
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1c7a3ca6628443dcb4c98252b3a6a2e2
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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