Potassium Cyanide → 3-Pyridineacetonitrile, 6-(trifluoromethyl)-

HRID 512136

반응식

HRID 512136 반응식
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][CH:8]=1.[C-:13]#[N:14].[K+]>C(O)C.O>[F:10][C:9]([F:12])([F:11])[C:6]1[N:7]=[CH:8][C:3]([CH2:2][C:13]#[N:14])=[CH:4][CH:5]=1

참가 물질

5

반응물 2

HCID 9032Potassium CyanideHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridine

생성물 1

HCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-수율 75%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

5-Chloromethyl-2-trifluoromethylpyridine (19.5 g, 99.7 mmol) in ethanol (160 mL) was added to a solution of potassium cyanide (9.74 g, 150 mmol) in water (80 mL) at 90° C. over 30 minutes. The mixture was stirred at 90° C. for 3 hours. Most of the ethanol was removed under reduced pressure and the aqueous layer was extracted with AcOEt (3×100 mL). The combined organic extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% AcOEt in hexanes) to afford (6-trifluoromethylpyridin-3-yl)-acetonitrile as a brown oil (9.79 g, 75%). 1H NMR (400 MHz, CDCl3) δ ppm 8.63 (s, 1 H), 7.90 (d, J=8.0 Hz, 1 H), 7.70 (d, J=8.0 Hz 1 H), 3.88 (s, 2 H). 19F NMR (400 MHz, CDCl3):168 cm−1. MS m/z 187.14

후처리

  1. customMost of the ethanol was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with AcOEt (3×100 mL)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (30% AcOEt in hexanes)

출처 및 근거

ORD 기록
ord-7072f7350d2b4bf6a701e027131eb1e4
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102591B2

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