Methyl 4-bromo-3,5-dimethoxybenzoate → Methyl 4-[1-(ethoxy)ethenyl]-3,5-dimethoxybenzoate

HRID 1096987ノート

反応式

HRID 1096987 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1Br)[C:6]([O:8][CH3:9])=[O:7].[F-].[K+].[CH2:18]([O:20][C:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22])[CH3:19]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:20][C:18]([C:12]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[O:14][CH3:15])=[CH2:19])[CH3:22]

参加物

6

反応物 3

HCID 117713Methyl 4-bromo-3,5-dimethoxybenzoateHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

生成物 1

HCID 57930895Methyl 4-[1-(ethoxy)ethenyl]-3,5-dimethoxybenzoate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

Methyl 3,5-dimethoxy-4-bromobenzoate (500 mg) was dissolved in toluene in a nitrogen atmosphere, and 1-ethoxyvinyltributyltin (742 μL) and tetrakis(triphenylphosphine)palladium (211 mg) were added to it, and stirred overnight at 110° C. The reaction liquid was cooled to room temperature, then aqueous potassium fluoride solution was added to it, and stirred at room temperature. The reaction liquid was filtered through Celite, the Celite was washed with ethyl acetate, and the filtrate was washed with saturated saline water. The organic layer was dried with sodium sulfate, the sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 85/15) to obtain the title compound.

後処理

  1. additionwere added to it
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. stirringstirred at room temperature
  5. customThe reaction liquid
  6. filtrationwas filtered through Celite
  7. washthe Celite was washed with ethyl acetate
  8. washthe filtrate was washed with saturated saline water
  9. dry with materialThe organic layer was dried with sodium sulfate
  10. customthe sodium sulfate was removed through filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 85/15)

出典と根拠

ORDレコード
ord-1c77621153e84b4ca2a4d1031262b5fe
出典データセット
uspto-grants-2012_03
特許番号
US08138197B2

反応ノート

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