Imidazole → HCID 66977751, compound

HRID 1255816Notes

Reaction equation

HRID 1255816 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][CH2:7][OH:8].N1C=CN=C1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][CH2:7][O:8][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 105367272-(3-BroMo-phenoxy)-ethanol

Product 1

HCID 66977751HCID 66977751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-Bromo-phenoxy)-ethanol (2.0 g, 9.2 mol) in dichloromethane (15 mL) at ice water bath temperature was added (1.25 g, 1.84 mmol) imidazole followed by the addition of TBSCl (1.67 g, 11 mmol) under nitrogen protection. TLC showed reaction was complete in 1 h. The reaction mixture was filtered. The filtrate was washed with water and dried over Na2SO4. The crude product was purified by column chromatography eluted with hexanes/ethyl acetate to afford titled product as a light color oil (2.65 g, 87%).

Workup

  1. customreaction
  2. filtrationThe reaction mixture was filtered
  3. washThe filtrate was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by column chromatography
  6. washeluted with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-0da2bdfd86d948c7bb0442f9022e71fd
Source dataset
uspto-grants-2013_06
Patent number
US08461157B2

Reaction notes

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