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

HRID 2120155Notes

Reaction equation

HRID 2120155 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:17](=[O:18])[CH2:16][O:15][C:14]=2[CH:19]=1.N1C=CN=C1.CCCCCC>CN(C)C=O.CCOCC>[Si:5]([O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:17](=[O:18])[CH2:16][O:15][C:14]=2[CH:19]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8058HexaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 234389036-((Tert-butyldimethylsilyl)oxy)benzofuran-3(2H)-oneYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

t-butyldimethylchlorosilane (3.6 g, 23.88 mmol) was added to a solution of 6-hydroxy-2,3-dihydrobenzo[b]furan-3-one (3.0 g, 19.98 mmol) and imidazole (2.0 g, 29.38 mmol) in N,N-dimethylformamide (DMF) (30 ml) under cooling with ice. The mixture was warmed to room temperature and stirred for 40 minutes. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with water, with diluted hydrochloric acid, with saturated aqueous solution of sodium bicarbonate, and then with saturated brine (aqueous solution of sodium chloride), sequentially, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The oily residue obtained was charged to silica gel column chromatography (hexane:ether=3:1) to obtain a yellow waxy product of 6-t-butyldimethylsilyloxy-2,3- dihydrobenzo[b]furan-3-one (4.3 g, 82%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe resulting residue was diluted with ethyl acetate
  4. washwashed with water, with diluted hydrochloric acid, with saturated aqueous solution of sodium bicarbonate
  5. dry with materialwith saturated brine (aqueous solution of sodium chloride), sequentially, and dried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe oily residue obtained

Sources & evidence

ORD record
ord-f806d85ba72648a78d4768a5592c3536
Source dataset
uspto-grants-2004_02
Patent number
US06689798B2

Reaction notes

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