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Toluene → Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate

HRID 2191904
ノート
印刷プレビュー

反応式

HRID 2191904 の反応式
Br[CH2:2][CH2:3]Br.[OH-].[Na+].C1(C)C=CC=CC=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24])#[N:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1([C:23]([O:25][CH3:26])=[O:24])[CH2:3][CH2:2]1)#[N:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 1512623Methyl(2-cyanophenyl)acetate

生成物 1

HCID 59470618Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate収率 65.3%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide
触媒
HCID 962Water溶媒

実験手順

Tetra-n-butylammonium bromide (1.5 g), 1,2-dibromoethane (6.5 g) and aqueous 50% sodium hydroxide solution (20 mL) were added to a toluene (40 mL) solution of methyl 2-cyanophenylacetate (4.0 g), and stirred at room temperature for 1 hour. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, then dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to give the entitled compound as a colorless solid (3.0 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-6113038d1c54459594a4643a827c32ea
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329711B2

反応ノート

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