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Sodium Carbonate → 5-Hydroxy-[1,1'-biphenyl]-3-carbaldehyde

HRID 30619
ノート
印刷プレビュー

反応式

HRID 30619 の反応式
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.N1C=CC=CC=1>[OH:10][C:8]1[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=[C:2]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 943653,5-Dihydroxybenzaldehyde

生成物 1

HCID 858888835-Hydroxy-[1,1'-biphenyl]-3-carbaldehyde

試薬・触媒・溶媒 5

HCID 178418476HCID 178418476、化合物
触媒
HCID 962Water溶媒
HCID 1049Pyridine溶媒2 回
HCID 6344Dichloromethane溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of 3,5-dihydroxybenzaldehyde (14.4 mmol) and pyridine (114 mmol) in methylene chloride (20 ml) was slowly added trifluoromethanesulfonic anhydride (36.2 mmol) keeping the temperature below 5° C. After 10 min the mixture was washed with water and the organic phase was concentrated under reduced pressure. The crude brown crystals (6.4 g—product and pyridine −1:1), phenylboronic acid (13.2 mmol), sodium carbonate (39.6 mmol) and dichlorobis(triphenylphosphine)-palladium (II). (3 mol %) was dissolved in DME (40 ml) and water (20 ml). The mixture was refluxed for 17 h under Argon, cooled to room temperature and extracted with ethyl acetate. Purification by chromatography yielded 5-Hydroxy-biphenyl-3-carbaldehyde

後処理

  1. customthe temperature below 5° C
  2. washAfter 10 min the mixture was washed with water
  3. concentrationthe organic phase was concentrated under reduced pressure
  4. temperatureThe mixture was refluxed for 17 h under Argon
  5. extractionextracted with ethyl acetate
  6. customPurification by chromatography

出典と根拠

ORDレコード
ord-473f15d3152d4cb6b61fa8db3a5f3858
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07423181B2

反応ノート

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