Imidazole → HCID 54323625, compound

HRID 1450256Notes

Reaction equation

HRID 1450256 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1)#[N:2].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].CN(C1C=CC=CN=1)C>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 54323625HCID 54323625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of 2-(4-cyanophenyl)ethanol are introduced into 50 ml of dimethylforamide. 2.54 g of imidazole, 5,63 g of tert-butyldimethylsilyl chloride and a spatula tip-ful of dimethylaminopyridine are added. The reaction medium is left for 2 hours at room temperature and is then added to an ice-water mixture. The mixture is extracted with ethyl acetate and the extracts dried over anhydrous sodium sulphate. The product is purified by chromatography on a column of silica gel, using a mixture of cyclohexane and ethyl acetate (10:1 v/v) as eluent, to give 1-cyano-4-(tert -butyldimethylsilyloxyethyl)benzene.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. dry with materialthe extracts dried over anhydrous sodium sulphate
  3. customThe product is purified by chromatography on a column of silica gel
  4. additiona mixture of cyclohexane and ethyl acetate (10:1 v/v) as eluent

Sources & evidence

ORD record
ord-9f0468086ecb420285732ae168a00dc8
Source dataset
uspto-grants-1997_02
Patent number
US05602132

Reaction notes

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