Imidazole → 1-(5-{[Tert-butyl(dimethyl)silyl]oxy}-1-benzofuran-2-yl)ethanone

HRID 1888716Notes

Reaction equation

HRID 1888716 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=2[CH:13]=1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C>[Si:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=2[CH:13]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 32378771-(5-Hydroxy-1-benzofuran-2-yl)ethanone

Product 1

HCID 580474981-(5-{[Tert-butyl(dimethyl)silyl]oxy}-1-benzofuran-2-yl)ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 1-(5-hydroxy-1-benzofuran-2-yl)ethanone (1.15 g, 6.53 mmol), DMF (10 mL), tert-butyldimethylchlorosilane (1.07 g, 7.18 mmol) and imidazole (666 mg, 9.80 mmol), an operation in the same manner as in Reference Example 16 was performed to give the title compound (1.76 g, yield 98%).

Sources & evidence

ORD record
ord-a4c90fe9f12449ae9ac57b8666de2454
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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