Thionyl Chloride → Methyl 5-cyano-2-methoxybenzoate

HRID 343528

反応式

HRID 343528 の反応式
CO[C:3]1C=C[C:11]([CH:14]=[O:15])=[CH:10][C:4]=1[C:5](=[N:8]O)OC.S(Cl)(Cl)=O.[C:20]([O:23][CH2:24]C)(=[O:22])[CH3:21].[CH3:26]CCCCC>ClCCl>[CH3:26][O:15][C:14]1[CH:11]=[CH:10][C:4]([C:5]#[N:8])=[CH:3][C:21]=1[C:20]([O:23][CH3:24])=[O:22]

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 21226206Ethyl acetate hexaneHCID 86583897Methyl 2-methoxy-5-formylbenzoate oxime

生成物 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Combine methyl 2-methoxy-5-formylbenzoate oxime (3.5 g, 16.7 mmol) in dichloromethane (75 mL) and cool in an ice-bath. Add dropwise thionyl chloride (2.0 mL, 27.2 mmol). After 20 minutes, dilute the reaction mixture with dichloromethane and extract with a saturated aqueous solution of sodium bicarbonate and then brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give methyl 2-methoxy-5-cyanobenzoate.

後処理

  1. extractionextract with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto give a residue

出典と根拠

ORDレコード
ord-9e709eaa0bab4f4f9b48bd7ef127e42b
出典データセット
uspto-grants-1999_01
特許番号
US05861417

関連ノート

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