Ethanol → [4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol

HRID 629389노트

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HRID 629389 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.FC(F)(F)S(O[C:18]1[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[CH3:23][N:20]1[CH:21]=[CH:22][C:18]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[N:19]1

참가 물질

9

반응물 4

HCID 702EthanolHCID 10796Cesium carbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 1170595431-methyl-1H-pyrazol-3-yl trifluoromethanesulfonate

생성물 1

HCID 24229469[4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol수율 27.2%

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of [4-(hydroxymethyl)phenyl]boronic acid (4.46 g), 1-methyl-1H-pyrazol-3-yl trifluoromethanesulfonate (4.50 g), cesium carbonate (19.1 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.80 g) in toluene (15.0 mL)-ethanol (1.00 mL)-water (1.00 mL) was subjected to microwave irradiation at 150° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, and the insoluble substance was removed by filtration. The filtrate was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.00 g).

후처리

  1. customirradiation at 150° C. for 1 hr
  2. customthe insoluble substance was removed by filtration
  3. washThe filtrate was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-19fc2cfce19b48379ea0303436522e96
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315458B2

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