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

HRID 629389ノート

反応式

HRID 629389 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-19fc2cfce19b48379ea0303436522e96
出典データセット
uspto-grants-2016_04
特許番号
US09315458B2

反応ノート

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