Imidazole → 6-((Tert-butyldimethylsilyl)oxy)benzofuran-3(2H)-one

HRID 869863Notes

Reaction equation

HRID 869863 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.[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>ClCCl>[Si:16]([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)([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 234389036-((Tert-butyldimethylsilyl)oxy)benzofuran-3(2H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxybenzofuran-3(2H)-one (30.0 g, 200 mmol) in dichloromethane (500 mL) was added TBSCl (36.0 g, 240 mmol) and imidazole (16.3 g, 240 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 h. The solvent was removed under reduced pressure to afford 6-(tert-butyldimethylsilyloxy)benzofuran-3(2H)-one (40.0 g, 80% yield), that was used directly in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2756e84fd4b746c7994e19382a80fabd
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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