Imidazole → HCID 59621119, compound

HRID 2061327Notes

Reaction equation

HRID 2061327 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.N1C=CN=C1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 59621120HCID 59621120, compound

Product 1

HCID 59621119HCID 59621119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cooled solution of 4-(5-iodo-2-methyl-benzyl)phenol (12.0 g) and imidazole (3.2 g) in dimethylformamide (40 mL) is added tert-butyldimethyl-chlorosilane (6.1 g). The ice-bath is removed and the solution is stirred at ambient temperature overnight. The solution is diluted with ethyl acetate and washed twice with hydrochloric acid (1 mol/L). The organic phase is dried (sodium sulphate) and concentrated in vacuo. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0->20:1).

Workup

  1. customThe ice-bath is removed
  2. additionThe solution is diluted with ethyl acetate
  3. washwashed twice with hydrochloric acid (1 mol/L)
  4. dry with materialThe organic phase is dried (sodium sulphate)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0->20:1)

Sources & evidence

ORD record
ord-ba47562095f7408393ff730518ebe1be
Source dataset
uspto-grants-2012_10
Patent number
US08283326B2

Reaction notes

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