Imidazole → 4-(Tert-butyldimethylsilyloxyethyl)-pyridine

HRID 345339

Reaction equation

HRID 345339 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7](O)[CH3:8])=[CH:3][CH:2]=1.Cl[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.C(OCC)(=[O:25])C.CCCCCC>CN(C)C=O>[Si:11]([O:25][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 90919alpha-Methyl-4-pyridinemethanolHCID 21226206Ethyl acetate hexane

Product 1

HCID 223216194-(Tert-butyldimethylsilyloxyethyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 16.3 g of 4-pyridylethanol, 21.8 g of chloro-tert-butyl-dimethylsilane and 10.9 g of imidazole in 150 ml of dimethylformamide is stirred 1 hour at room temperature. The product is isolated by extraction into ethyl acetate/hexane (1:1) and washed 4 times with 400 ml of water; the extract is filtered through silica gel and concentrated in vacuo to yield 4-(tert-butyl-dimethylsilyloxyethyl)-pyridine.

Workup

  1. washwashed 4 times with 400 ml of water
  2. filtrationthe extract is filtered through silica gel
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d115594940142cea789a0e5465f75f0
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Linked notes

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