Imidazole → tert-Butyl-[2-(5-ethyl-furan-2-yl)-ethoxy]-dimethyl-silane

HRID 2110433Notes

Reaction equation

HRID 2110433 reaction equation
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH2:14]([C:16]1[O:17][C:18]([CH2:21][CH2:22][OH:23])=[CH:19][CH:20]=1)[CH3:15]>CN(C=O)C.C(OCC)C>[C:7]([Si:10]([O:23][CH2:22][CH2:21][C:18]1[O:17][C:16]([CH2:14][CH3:15])=[CH:20][CH:19]=1)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:6]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 218749232-Ethyl-5-(2-hydroxyethyl)furan

Product 1

HCID 21875390tert-Butyl-[2-(5-ethyl-furan-2-yl)-ethoxy]-dimethyl-silaneYield 80.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Imidazole (255 mg, 3.75 mmol) and TBSCl (414 mg, 2.75 mmol) were added to the solution of 245A (350 mg, 2.5 mmol) in DMF (4 mL). The mixture was stirred at rt for 15 hr and then 100 mg (0.66 mmol) of additional TBSCl was added to drive the reaction to completion. After stirring for an additional hour, the reaction mixture was diluted with diethylether (100 mL) and washed with water (20 mL), 1 N HCl (20 mL), water (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give 509 mg of compound 434A (80.3%) as a yellow oil.

Workup

  1. customthe reaction to completion
  2. stirringAfter stirring for an additional hour
  3. washwashed with water (20 mL), 1 N HCl (20 mL), water (20 mL) and brine (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1008b6c1b3d45f9a747479c212ebb67
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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