Ammonium Chloride → Ethyl (2E,4E)-2-azido-5-(2,6-dimethoxyphenyl)penta-2,4-dienoate

HRID 1639887

反応式

HRID 1639887 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1/[CH:11]=[CH:12]/[CH:13]=O.[N:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N+:16]=[N-:17].[Na].[Cl-].[NH4+]>C(O)C.CCO.CCO>[N:15](/[C:18](=[CH:13]/[CH:12]=[CH:11]/[C:4]1[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N+:16]=[N-:17]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545SodiumHCID 23928193(2E)-3-(2,6-dimethoxyphenyl)acrylaldehyde

生成物 1

HCID 86637359Ethyl (2E,4E)-2-azido-5-(2,6-dimethoxyphenyl)penta-2,4-dienoate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 57419690EtOH Ethanol溶媒

反応条件

温度
-10 °C

実験手順

Add dropwise, while stirring, a solution of 37 g (192 mmol) of (2E)-3-(2,6-dimethoxyphenyl)acrylaldehyde and 85.7 g (664 mmol) of ethyl 2-azidoacetate in 200 mL of absolute ethanol EtOH to a solution of 15.5 g (673 mmol) of sodium in 500 mL of absolute EtOH cooled to −10° C. and kept under argon, maintaining the temperature at −10° C. After stirring at −10° C. for 3 h, stir the reaction mixture for 15 h at RT, then pour into 600 mL of an aqueous solution of ammonium chloride (NH4Cl) at 30 wt. %. After filtration on a frit and rinsing with 2×200 mL of water, take up the precipitate in 600 mL of DCM, dry over Na2SO4 and concentrate under reduced pressure, which leads to 42 g of ethyl (2E,4E)-2-azido-5-(2,6-dimethoxyphenyl)penta-2,4-dienoate in the form of a yellow solid.

後処理

  1. additionAdd dropwise
  2. stirringAfter stirring at −10° C. for 3 h
  3. stirringstir the reaction mixture for 15 h at RT
  4. filtrationAfter filtration on a frit
  5. washrinsing with 2×200 mL of water
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate under reduced pressure, which

出典と根拠

ORDレコード
ord-b55a78e8229d448bb0dc1dd34a2ae4b4
出典データセット
uspto-grants-2012_02
特許番号
US08110579B2

関連ノート

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