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Potassium Carbonate → 3-(4-Ethoxycarbonylphenyl)phenol

HRID 2307542
ノート
印刷プレビュー

反応式

HRID 2307542 の反応式
COC[O:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1.I[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[OH:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=2)[CH:8]=[CH:9][CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 22606941(3-(Methoxymethoxy)phenyl)boronic acid

生成物 1

HCID 226069053-(4-Ethoxycarbonylphenyl)phenol

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

2 g of 3-methoxymethoxyphenylboronic acid (13.3 mmol) and 1.86 mL (11 mmol) of ethyl 4-iodobenzoate are dissolved in 20 mL of DME. 13.3 mL of 2M potassium carbonate solution (26.6 mmol) are then added and the reaction medium is degassed with a stream of argon for 10 minutes. 640 mg of Pd(PPh3)4 are then added and the mixture is heated at 90° C. for 14 hours. After treatment with saturated ammonium chloride solution, extraction with ethyl acetate and then drying and evaporation of the solvents from the organic phase, the residue is dissolved in 25 mL of anhydrous methanol and 0.5 mL of sulphuric acid is then added; The reaction medium is refluxed for 15 h and then cooled and finally treated by addition of water. After extraction with ethyl acetate, the organic phase is separated out by settling, dried and then concentrated under reduced pressure. After purification by chromatography on a column of silica, a colourless oil is obtained (m=2 g; Y=75%). (

後処理

  1. customthe reaction medium is degassed with a stream of argon for 10 minutes
  2. addition640 mg of Pd(PPh3)4 are then added
  3. extractionAfter treatment with saturated ammonium chloride solution, extraction with ethyl acetate
  4. customdrying
  5. customevaporation of the solvents from the organic phase
  6. dissolutionthe residue is dissolved in 25 mL of anhydrous methanol
  7. addition0.5 mL of sulphuric acid is then added
  8. temperatureThe reaction medium is refluxed for 15 h
  9. temperaturecooled
  10. additionfinally treated by addition of water
  11. extractionAfter extraction with ethyl acetate
  12. customthe organic phase is separated out
  13. customdried
  14. concentrationconcentrated under reduced pressure
  15. customAfter purification by chromatography on a column of silica
  16. customa colourless oil is obtained (m=2 g; Y=75%)

出典と根拠

ORDレコード
ord-b031d875407645659002fa50b65b1fc0
出典データセット
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06831106B1

反応ノート

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