Triethylamine → Methanesulfonic acid pyridin-2-ylmethyl ester

HRID 547589Notes

Reaction equation

HRID 547589 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].C(N(CC)CC)C.[S:16](Cl)([CH3:19])(=[O:18])=[O:17]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][S:16]([CH3:19])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11474PiconolHCID 31297Methanesulfonyl chloride

Product 1

HCID 22417657Methanesulfonic acid pyridin-2-ylmethyl esterYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-pyridylcarbinol (10) (300 mg, 2.70 mmol) and triethyl amine (698 mg, 6.75 mmol) in dry THF (10 mL) at 0° C. was added a solution of mesylchloride (470 mg, 4.1 mmol) in dry THF (10 mL). Reaction mixture was allowed to stir for 2 h at room temperature [reaction was followed by TLC]. Reaction mixture was concentrated to remove THF under reduced pressure and the residue was dissolved in CH2Cl2 (100 mL), washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give compound 11 (300 mg, 59%) as gum and it was taken as such for next step.

Workup

  1. customReaction mixture
  2. custom[reaction was followed by TLC]
  3. customReaction mixture
  4. concentrationwas concentrated
  5. customto remove THF under reduced pressure
  6. dissolutionthe residue was dissolved in CH2Cl2 (100 mL)
  7. washwashed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09c6bf44197444038b50093c44d0d312
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Reaction notes

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