Imidazole → HCID 66977751, compound

HRID 1399943Notes

Reaction equation

HRID 1399943 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-2c71311c803c473a8c5b24b5c0f23521
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

Loading…