Allyl bromide → 2-Benzyloxy-5-[(2-propenyl)oxy]benzaldehyde

HRID 412166ノート

反応式

HRID 412166 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[CH:25]=[CH2:26].CCOC(C)=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH:25]=[CH2:24])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 185361922-(Benzyloxy)-5-hydroxybenzaldehyde

生成物 1

HCID 185361832-Benzyloxy-5-[(2-propenyl)oxy]benzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of the product from Step A (75.4 mmol) in 100 mL of DMF was added potassium carbonate (20.8 g, 150.7 mmol), followed by allyl bromide (11.7 mL, 135 mmol). The reaction was warmed to 60° C. and stirred for one hour. The solution was poured into EtOAc and washed with water, saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (20-30% EtOAc/hexane) to provide the titled product, along with unreacted starting material (4.39 g, 26%).

後処理

  1. washwashed with water, saturated NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting product was purified by silica gel chromatography (20-30% EtOAc/hexane)

出典と根拠

ORDレコード
ord-1b40a4cf657d453cb3e06a20ba23ab57
出典データセット
uspto-grants-2003_05
特許番号
US06562823B1

反応ノート

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