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

HRID 2113132노트

반응식

HRID 2113132 반응식
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]

참가 물질

8

반응물 3

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

생성물 1

HCID 223911924-Ethyl-3-(pyridin-3-yl)benzaldehyde수율 49.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-52f2ff7d43c54a38807e952620733d2b
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524873B2

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