Imidazole → 6-Triisopropylsilanyloxy-benzofuran-3-one

HRID 556361Notes

Reaction equation

HRID 556361 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.N1C=CN=C1.Cl[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].CCOC(C)=O>CN(C=O)C.O>[CH:19]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1)([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 139400Triisopropylsilyl chlorideHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 669926146-Triisopropylsilanyloxy-benzofuran-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 9.8 g (65.3 mMol) 6-hydroxy-2H-benzofuran-3-one in 80 ml DMF, 10.6 g (157 mMol) imidazole and 16.6 ml (78.3 mMol) chloro-triisopropylsilane are added dropwise. After 1 h, the mixture is poured into 300 ml EtOAc and 300 ml water, the aq. phase is separated off and extracted with 3×100 ml EtOAc. The organic layers are washed 4 times with 10% citric acid solution, brine and dried (Na2SO4). Then char coal is added. Filtration, concentration and drying (10 mbar, 65-85° C.) give the oily title compound: MS: [M+1]+=307; TLC(hexane/EtOAc 2:1): Rf=0.61.

Workup

  1. customthe aq. phase is separated off
  2. extractionextracted with 3×100 ml EtOAc
  3. washThe organic layers are washed 4 times with 10% citric acid solution, brine
  4. dry with materialdried (Na2SO4)
  5. additionThen char coal is added
  6. filtrationFiltration, concentration
  7. customdrying (10 mbar, 65-85° C.)

Sources & evidence

ORD record
ord-0c34756aac85403aa90619b5d22c92e9
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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