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

HRID 1097861ノート

反応式

HRID 1097861 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+].

後処理

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

出典と根拠

ORDレコード
ord-1c7a3ca6628443dcb4c98252b3a6a2e2
出典データセット
uspto-grants-2012_03
特許番号
US08143280B2

反応ノート

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