Imidazole → tert-Butyl[(2-iodophenyl)methoxy]dimethylsilane

HRID 984521Notes

Reaction equation

HRID 984521 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CN=C1.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C=O)C>[CH3:15][C:16]([Si:19]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[I:1])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 1076292-Iodobenzylic alcohol

Product 1

HCID 17755788tert-Butyl[(2-iodophenyl)methoxy]dimethylsilaneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-iodobenzylalcohol (2.34 g, 10 mmol) in 50 mL DMF was added imidazole (1.02 g, 15 mmol, 1.5 equiv) and TBSCl (1.66 g, 11 mmol, 1.1 equiv). The mixture was stirred at room temperature for 5 h, then 40 mL of water was added. The mixture was transferred to a separatory funnel. The aqueous layer was separated and extracted with ether (2×40 mL). The combined organic layers were then washed with water (2×40 mL), dried with MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography and then Kugelrohr distillation to afford the product (3.107 g, 89%) as a clear colorless liquid.

Workup

  1. customThe mixture was transferred to a separatory funnel
  2. customThe aqueous layer was separated
  3. extractionextracted with ether (2×40 mL)
  4. washThe combined organic layers were then washed with water (2×40 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography
  9. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-c106af8863204f7e8eaa8b4f68b51608
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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