Imidazole → 3-(Benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-chloropyridine

HRID 709777Notes

Reaction equation

HRID 709777 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=[N:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([Cl:15])=[N:13][CH:12]=[C:11]([CH2:16][O:17][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 117760270(5-(Benzyloxy)-6-chloropyridin-3-yl)methanol

Product 1

HCID 1317339153-(Benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-chloropyridineYield 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-(benzyloxy)-6-chloropyridin-3-yl)methanol (1.76 g) and tert-butyldimethylchlorosilane (1.59 g) in DMF (10 mL) was added imidazole (960 mg), and the mixture was stirred at room temperature for 14 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.64 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6604187d3659418d81865fd301b616f3
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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