2,6-Dichloropyridine → 2-Chloro-6-(2-Thienylmethoxy)Pyridine

HRID 55118

Reaction equation

HRID 55118 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].[H-].[Na+].[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Cl)[N:12]=1>O1CCCC1>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[N:12]=1

Participants

5

Reactant 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 694672-Thiophenemethanol

Product 1

HCID 181869442-Chloro-6-(2-Thienylmethoxy)Pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 2-thiophenemethanol (1.5 g, 0.0135×1.0 mol) and sodium hydride (0.58 g, (ca.60% in mineral oil), 0.0135×1.1 mol) in tetrahydrofuran, 2,6-dichloropyridine (2.0 g, 0.0135 mol) was added and the resultant solution was refluxed for about 2 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate. The obtained organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and thereafter, concentrated and purified on a silica gel column to obtain the end product.

Workup

  1. additionwas added
  2. customThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  3. washThe obtained organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified on a silica gel column
  7. customto obtain the end product

Sources & evidence

ORD record
ord-03751012921c4d36a4cff78637b58504
Source dataset
uspto-grants-1997_04
Patent number
US05624942

Linked notes

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