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

HRID 412166

반응식

HRID 412166 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-1b40a4cf657d453cb3e06a20ba23ab57
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562823B1

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