Water → 4-(4-Hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile

HRID 1890386노트

반응식

HRID 1890386 반응식
[C@H:1]1([OH:8])[CH2:6][CH2:5][C@H:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1.O>CS(C)=O.C(OCC)C>[OH:7][CH:4]1[CH2:5][CH2:6][CH:1]([O:8][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:21])([F:23])[F:22])[CH:13]=2)[CH2:2][CH2:3]1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 178521615HCID 178521615, 화합물

생성물 1

HCID 672831644-(4-Hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile수율 60%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 3283Diethyl Ether용매

실험 절차

Trans-cyclohexane-1,4-diol (4.30 mmol) and sodium hydride (60% suspension in oil, 2.15 mmol) are suspended in dry dimethylsulfoxide (4 mL) and a solution of 4-fluoro-2-trifluoromethyl-benzonitrile (2.15 mmol) in dry dimethylsulfoxide (4 mL) is added dropwise. The resulting mixture is stirred at room temperature. After 1 hour reaction time, the reaction is treated with water (10 mL), the precipitate formed is separated by filtration and the filtrate is extracted with dichloromethane (25 mL). The organic phase is washed with aqueous saturated ammonium chloride (5 mL), dried over magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The precipitate is triturated with diethylether (15 mL), filtered and the filtrate concentrated under reduced pressure. Both fractions of crude product are combined, dissolved in dichloromethane and purified by chromatography through a short pad of silica gel (dichloromethane and then diethylether as eluents) to afford the desired product (60% yield).

후처리

  1. customAfter 1 hour reaction time
  2. customthe precipitate formed
  3. customis separated by filtration
  4. extractionthe filtrate is extracted with dichloromethane (25 mL)
  5. washThe organic phase is washed with aqueous saturated ammonium chloride (5 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe precipitate is triturated with diethylether (15 mL)
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated under reduced pressure
  12. dissolutiondissolved in dichloromethane
  13. custompurified by chromatography through a short pad of silica gel (dichloromethane

출처 및 근거

ORD 기록
ord-1d950f66917b49cf971be5ce2511c19b
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507474B2

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