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

HRID 333763노트

반응식

HRID 333763 반응식
[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]

참가 물질

5

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilane2회HCID 11726816Tetrabutylammonium Fluoride Trihydrate2회HCID 574213311-(2-Methyl-pyridin-4-yl)-2-phenyl-propan-1-one

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+].

후처리

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

출처 및 근거

ORD 기록
ord-828fc69cd2b94806ae9bd57d085856b6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883786B2

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