Triethylamine → 5-(CHLOROMETHYL)-2-ETHOXYPYRIDINE

HRID 2090289Notes

Reaction equation

HRID 2090289 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.CS([Cl:23])(=O)=O>C(Cl)Cl>[Cl:23][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10630706HCID 10630706, compound

Product 1

HCID 105351905-(CHLOROMETHYL)-2-ETHOXYPYRIDINE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Ethoxypyridin-3-yl)methanol (1.0 g, 6.5 mmol) was dissolved in methylene chloride (20 mL), and triethylamine (1.8 mL, 13 mmol) was added. The reaction mixture was cooled in an ice bath and methanesulfonyl chloride (0.67 mL, 8.6 mmol, Aldrich, Cat. 471259) was slowly added. The reaction mixture was stirred for 2 hours and then the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by flash chromatograph on a silica gel column using 20% Ethyl acetate in hexane as eluent to afford the desired compound. LCMS (M+H)+: m/z=172.2.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatograph on a silica gel column

Sources & evidence

ORD record
ord-a7ce2255f5184bf697b2612bf085f673
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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