Sodium Carbonate → 4-Ethyl-3-(pyridin-3-yl)benzaldehyde

HRID 2113132ノート

反応式

HRID 2113132 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH3:11])[CH:5]=[O:6].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+].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>[CH2:10]([C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:14]1[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=1)[CH3:11]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 222596893-Bromo-4-ethylbenzaldehyde

生成物 1

HCID 223911924-Ethyl-3-(pyridin-3-yl)benzaldehyde収率 49.4%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of 3-bromo-4-ethylbenzaldehyde (2.45 g, 0.0115 mol), pyridine 3-boronic acid (1.42 g, 0.0115 mol, Matrix Scientific), 2M Na2CO3 (15 mL) in 30 mL of toluene was added 1.33 g of Pd (PPh3)4 (1.15 mmol, Aldrich). The mixture was then heated to 80 C under N2 for 16 hours. The mixture was cooled to RT and was diluted with 100 mL of EtOAc and 40 mL of sat. NaHCO3 aq. solution. The organic phase was washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude product was chromatographed (silica gel, 20% EtOAc in hexane) to provide yellow oil (1.2 g).

後処理

  1. temperatureThe mixture was then heated to 80 C under N2 for 16 hours
  2. washThe organic phase was washed with 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed (silica gel, 20% EtOAc in hexane)

出典と根拠

ORDレコード
ord-52f2ff7d43c54a38807e952620733d2b
出典データセット
uspto-grants-2009_04
特許番号
US07524873B2

反応ノート

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