Sodium Hydroxide → (Z)-2-(4-chloro-2-fluoro-phenyl)-4-cyclopropyl-but-2-enenitrile

HRID 909007ノート

反応式

HRID 909007 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.[CH:12]1([CH2:15][CH:16]=O)[CH2:14][CH2:13]1.[OH-].[Na+]>CC(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](=[CH:16]/[CH2:15][CH:12]2[CH2:14][CH2:13]2)/[C:7]#[N:8])=[C:4]([F:11])[CH:3]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileHCID 103078492-Cyclopropylacetaldehyde

生成物 1

HCID 58222867(Z)-2-(4-chloro-2-fluoro-phenyl)-4-cyclopropyl-but-2-enenitrile収率 50.1%

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) (3.39 g, 20.0 mmol) and cyclopropyl-acetaldehyde (Aldrich) (1.68.0 g, 20.0 mmol) in iPrOH (25 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 under reduced pressure to afford (Z)-2-(4-chloro-2-fluoro-phenyl)-4-cyclopropyl-but-2-enenitrile (2.36 g, 50.0%) 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 under reduced pressure

出典と根拠

ORDレコード
ord-d42bf023f270420f968cd00e202746ce
出典データセット
uspto-grants-2011_09
特許番号
US08017607B2

反応ノート

読み込み中…