Triethylamine → 5-(Chloromethyl)-2-methylpyridine

HRID 1295984Notes

Reaction equation

HRID 1295984 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=1.S([Cl:21])(C)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[Cl:21][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH3:8])=[N:14][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 122143385-(Chloromethyl)-2-methylpyridineYield 37.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (96 ml, 0.69 mol) was added to a solution of (6-methyl-3-pyridyl)methanol (28.4 g, 0.23 mol) in methylene chloride (230 ml) while cooling on ice. Mesyl chloride (26.8 ml, 0.35 mol) was then slowly added dropwise over a period of 20 minutes at the same temperature and the mixture was stirred for 10 hours while gradually raising the temperature to room temperature. After confirming completion of the reaction by thin layer chromatography, the mixture was diluted with ethyl acetate and poured into saturated aqueous NaHCO3. After separating the aqueous layer, extraction was performed with ethyl acetate, and the collected organic layer was washed with saturated aqueous NaCl and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to yield the title compound (12.2 g). This was used without further purification for the following reaction.

Workup

  1. temperaturewhile cooling on ice
  2. customcompletion of the reaction by thin layer chromatography
  3. customAfter separating
  4. extractionthe aqueous layer, extraction
  5. washthe collected organic layer was washed with saturated aqueous NaCl
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e3b3468ae3294f408a8e1e793ac922ce
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…