Sodium Hydroxide → (Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile

HRID 909006ノート

反応式

HRID 909006 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH:15]=O.[OH-].[Na+]>CC(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](=[CH:15]/[CH2:14][C:13]([CH3:18])([CH3:17])[CH3:12])/[C:7]#[N:8])=[C:4]([F:11])[CH:3]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 763353,3-DimethylbutanalHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrile

生成物 1

HCID 58222872(Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile収率 100.1%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-chloro-2-fluoro-benzyl cyanide (Oakwood) (1.70 g, 10.0 mmol) and 3,3-dimethyl-butyraldehyde (Aldrich) (1.0 g, 10.0 mmol) in iPrOH (20 mL) was added 2 N NaOH (2.0 mL) dropwise at rt and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and the organic layer was separated, washed with water, brine, dried over Na2SO4 and concentrated. The residue was dried overnight in vacuum to give (Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile (2.52 g, 100%) as a colorless oil which was used in the next step without further purification.

後処理

  1. customthe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was dried overnight in vacuum

出典と根拠

ORDレコード
ord-ea27718fa3c54615ae83a5cd6d291c9a
出典データセット
uspto-grants-2011_09
特許番号
US08017607B2

反応ノート

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