Malononitrile → (2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

HRID 1397196ノート

反応式

HRID 1397196 の反応式
FC(F)(F)S(O[CH2:7][C:8]([F:19])([F:18])[C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])(=O)=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>>[F:19][C:8]([F:18])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:12])[F:13])[CH2:7][CH:23]([C:22]#[N:26])[C:24]#[N:25]

参加物

4

反応物 3

HCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 27758912,2,3,3,4,4,5,5-Octafluoropentyl trifluoromethanesulfonate

生成物 1

HCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile収率 65%

実験手順

A mixture of compound 5b (15.0 g, 41.2 mmol), malononitrile (5.44 g, 82.4 mmol), and potassium carbonate (28.5 g, 206 mmol) in 1,2-dimethoxymethane (150 ml) was stirred overnight at room temperature under nitrogen. The reaction mixture was quenched with water (150 ml) and extracted with ethyl acetate (2×200 ml). The combined organic extracts were washed with brine (200 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 85:15 hexanes/EtOAc) to provide 2-(2,2,3,3,4,4,5,5-Octafluoropentyl)malononitrile (5c) (7.5 g, 65%) as a white solid:

後処理

  1. customThe reaction mixture was quenched with water (150 ml)
  2. extractionextracted with ethyl acetate (2×200 ml)
  3. washThe combined organic extracts were washed with brine (200 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, 85:15 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-56136604385748b694f8dc9c1b1fca33
出典データセット
uspto-grants-2014_12
特許番号
US08901170B2

反応ノート

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