Imidazole → 2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]furan

HRID 2378405Notes

Reaction equation

HRID 2378405 reaction equation
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[OH:14][CH2:15][CH2:16][C:17]1[O:18][CH:19]=[CH:20][CH:21]=1.CCOCC>CN(C=O)C>[CH3:6][C:7]([Si:10]([CH3:12])([CH3:11])[O:14][CH2:15][CH2:16][C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 6421102-Furanethanol

Product 1

HCID 218750272-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]furanYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (3.65 g, 53.6 mmol) and TBSCl (6.47 g, 42.9 mmol) were added to the solution of compound 255A (4.00 g, 35.7 mmol) in 50 mL of DMF. The mixture was stirred at rt for 2 h and then the reaction mixture was poured into ether. The ether solution was washed with water (1×), 1 N HCl (1×), water (1×) and brine (1×). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 30% CH2Cl2/70% hexane gave 7.4 g (32.7 mmol, 91.7%) of 255B as a colorless oil.

Workup

  1. washThe ether solution was washed with water (1×), 1 N HCl (1×), water (1×) and brine (1×)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel eluting with 30% CH2Cl2/70% hexane

Sources & evidence

ORD record
ord-62b7b0f7021d45d78cebf7823ba91264
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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