Imidazole → HCID 18706297, compound

HRID 1421860Notes

Reaction equation

HRID 1421860 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Br:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16].N1C=CN=C1>CN(C=O)C.O>[CH:1]([Si:4]([O:16][CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[Br:12])([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 728502-Bromobenzyl alcoholHCID 139400Triisopropylsilyl chloride

Product 1

HCID 18706297HCID 18706297, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Triisopropylsilyl chloride (8.0 ml, 46.0 mmol) was added dropwise to a solution of 2-bromobenzyl alcohol (7.0 g, 39.6 mmol) and imidazole (5.1 g, 75.0 mmol) in DMF (25 ml) and the resulting solution stirred at 20° C for 18 hours. The reaction mixture was diluted with water (400 ml) and extracted with ethyl acetate (3×75 ml). The combined organic extracts was washed with saturated brine (1×75 ml), dried (MgSO4) and concentrated to yield the title compound as a clear oil (10.2 g, 78%). 1H NMR (250 MHz, CDCl3) δ 1.05-1.24 (21 H, m), 4.82 (2 H, s), 7.11 (1 H, dt, J=7.5, 1.2), 7.34 (1 H, t, J=7.6), 7.48 (1 H, dd, J=7.9, 1.1), 7.63 (1 H, d, J=6.7).

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. washThe combined organic extracts was washed with saturated brine (1×75 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f182905c88a2470e98c848e5a9c44936
Source dataset
uspto-grants-2000_06
Patent number
US06080740

Reaction notes

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