Imidazole → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine

HRID 379906Notes

Reaction equation

HRID 379906 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C)C=O.C(OCC)C>[Si:15]([O:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2763647(2-Chloropyridin-3-yl)methanol

Product 1

HCID 183681113-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridineYield 73.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-3-(hydroxymethyl)pyridine (Read, M. W; and Ray, P. S.; J. Heterocyclic. Chem., 1995, 32, 1595-1597., 2.81 g, 19.1 mmol) and imidazole (3.25 g, 47.7 mmol) in N,N-dimethylformamide (30 ml) was added tert-butyldimethylsilyl chloride (3.74 g, 24.8 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 17 h. The solution was diluted with diethyl ether (200 ml), and the resulting solution was washed with water (100 ml×3), and dried (MgSO4). Removal of solvent gave an oily residue. Purification by flash column chromatography eluting with ethyl acetate/hexane (1:15) afforded 3.61 g (73%) of the title compound.

Workup

  1. washthe resulting solution was washed with water (100 ml×3)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent
  4. customgave an oily residue
  5. customPurification by flash column chromatography
  6. washeluting with ethyl acetate/hexane (1:15)

Sources & evidence

ORD record
ord-dc0a249198764f9aba7615da89fcbca4
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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