Imidazole → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2,6-dichloropyridine

HRID 1360703Notes

Reaction equation

HRID 1360703 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C=O)C>[Si:16]([O:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:10])=[CH:5][CH:6]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 12259932(2,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 577003633-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2,6-dichloropyridineYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2,6-dichloropyridin-3-yl)methanol (from Step A above, 6.3 g) in DMF was added imidazole (3.06 g) and t-butyldimethylsilyl chloride (6.02 g) at 0° C. The mixture was warmed to room temperature and stirred for 1 h before poured into water. The solution was extracted with ethyl acetate. The organic layer was washed with water (5×), brine, dried over MgSO4 and concentrated. The residue was purified by silica gel (hexanes/ethyl acetate) to give the title compound (8.7 g).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water (5×), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cc0c7b7303da4028b1a9331cab0e9f11
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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