Sodium Cyanide → [1-(4-Trifluoromethyl-phenyl)-cyclopentyl]-acetonitrile

HRID 2169281ノート

反応式

HRID 2169281 の反応式
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14]OS(C)(=O)=O)[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C-:22]#[N:23].[Na+]>CS(C)=O.O>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][C:22]#[N:23])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 86725929Methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester

生成物 1

HCID 86725930[1-(4-Trifluoromethyl-phenyl)-cyclopentyl]-acetonitrile収率 60%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

To a stirred solution of methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester (240) (7 g, 21.73 mmol) in dimethyl sulfoxide (200 mL) were added KI (0.361 g, 2.17 mmol) and NaCN (1.6 g, 32.6 mmol). The reaction mixture was then stirred at 140° C. for 6 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate (2×300 mL) and the organic layer was washed with water and brine. It was then dried over Na2SO4 and concentrated. The crude product was purified by 100-200 silica column chromatography using 5% ethyl acetate in hexane as the eluent to give [1-(4-trifluoromethyl-phenyl)-cyclopentyl]-acetonitrile (241) (3.3 g, 60%) as a colorless thick liquid.

後処理

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (2×300 mL)
  3. washthe organic layer was washed with water and brine
  4. dry with materialIt was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by 100-200 silica column chromatography

出典と根拠

ORDレコード
ord-f03ae4344a5641268f4f39aca83a122e
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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