Imidazole → HCID 11817742, compound

HRID 407194Notes

Reaction equation

HRID 407194 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[C:10]([Si:14]([CH3:17])([CH3:16])Cl)([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C.O>[Si:14]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 11817742HCID 11817742, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-chloropyridin-4-yl)methanol (0.307 g, 2.14 mmol) in 20 mL of DMF at 0° C. under an atmosphere of nitrogen was added tert-butyldimethylchlorosilane (0.355 g, 2.35 mol) and imidazole (0.160 g, 2.35 mmol). After 1 h, the mixture was diluted with water, washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was subjected to silica gel chromatography eluting with 0-15% EtOAc in hexanes to provide 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine that gave a mass ion (ES+) of 258.1 for [M+H]+.

Workup

  1. washwashed 3× with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washeluting with 0-15% EtOAc in hexanes

Sources & evidence

ORD record
ord-700dce9cc7b346489f66fa4cb3ac8889
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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