Water → Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate

HRID 1169353ノート

反応式

HRID 1169353 の反応式
[O-]CC.[Na+].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16].O>C(O)C.C1(C)C=CC=CC=1>[N:14](/[C:17](=[CH:10]\[C:9]1[CH:12]=[CH:13][C:6]([Br:5])=[CH:7][CH:8]=1)/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16]

参加物

7

反応物 4

HCID 962WaterHCID 69480Acetic acid, azido-, ethyl esterHCID 707414-BromobenzaldehydeHCID 2723922Sodium ethoxide

生成物 1

HCID 24767341Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate収率 39%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒2 回

実験手順

Into a solution of sodium ethoxide (a 20% solution in ethanol, 22.2 g) in toluene (100 ml) was added at 0° C. over a period of more than 10 minutes a solution of 4-bromobenzaldehyde (10 g) and ethyl azidoacetate (7.0 g) in toluene (50 ml). After being stirred at room temperature for 2 hours, the reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate/hexane 1:19) to obtain ethyl (Z)-2-azido-3-(4-bromophenyl)acrylate (6.24 g) as a yellow oily substance.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialwas dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was subjected to separation and purification

出典と根拠

ORDレコード
ord-b5f4680863cc4c45a60cd640bde76739
出典データセット
uspto-grants-2003_09
特許番号
US06627651B1

反応ノート

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