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

HRID 629389Notes

Reaction equation

HRID 629389 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-19fc2cfce19b48379ea0303436522e96
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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