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

HRID 909007노트

반응식

HRID 909007 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d42bf023f270420f968cd00e202746ce
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017607B2

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