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Toluene → Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate

HRID 1891037
ノート
印刷プレビュー

反応式

HRID 1891037 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

1.5 g of tetra-n-butylammonium bromide, 6.5 g of 1,2-dibromoethane and 20 mL of aqueous 50% sodium hydroxide solution were added to a toluene (40 mL) solution of 4.0 g of methyl 2-cyanophenylacetate, 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, 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 obtain 3.0 g of the entitled compound as a colorless compound.

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-683bd5ef5ba6447ebc7da02601dbd704
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507504B2

反応ノート

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