Imidazole → 4-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile

HRID 1683067Notes

Reaction equation

HRID 1683067 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.CN(C=O)C.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]#[N:28])=[CH:22][CH:21]=1>CCOCC>[Si:1]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]#[N:28])=[CH:22][CH:21]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 265484-Hydroxybenzyl cyanideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 183335824-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine tert-butyldimethylsilyl chloride (0.460 mol), imidazole (0.600 mol) and DMF (125 mL). Add 4-hydroxyphenylacetonitrile (0.400 mol) and maintain at ambient temperature for 16 h. Dilute with ether (500 mL), extract with water (4×75 mL), saturated sodium chloride (75 mL), dry over MgSO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph on silica gel to obtain the title compound.

Workup

  1. extractionextract with water (4×75 mL), saturated sodium chloride (75 mL)
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-8493f9f6d3d2492c95b33db810e82e79
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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