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

HRID 512136

反応式

HRID 512136 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-7072f7350d2b4bf6a701e027131eb1e4
出典データセット
uspto-grants-2015_08
特許番号
US09102591B2

関連ノート

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