Methanesulfonyl chloride → Methanesulfonic acid 2-(pyridin-2-yloxy)-ethyl ester

HRID 448955Notes

Reaction equation

HRID 448955 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][OH:10].[CH3:11][S:12](Cl)(=[O:14])=[O:13].CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][O:10][S:12]([CH3:11])(=[O:14])=[O:13]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 122163042-(2-Hydroxyethoxy)pyridine

Product 1

HCID 86642582Methanesulfonic acid 2-(pyridin-2-yloxy)-ethyl esterYield 72.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Pyridin-2-yloxy)-ethanol (100 mg, 0.72 mmol) was dissolved in DCM (2 mL) and MsCl (72 μL, 0.94 mmol) and DIPEA (192 μL, 1.08 mmol) were added. The mixture was stirred at rt overnight, diluted with EtOAc, washed with water, sat. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 114 mg methanesulfonic acid 2-(pyridin-2-yloxy)-ethyl ester which was used without further purification for the next step.

Workup

  1. washwashed with water, sat. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43261eaf1a6b424283e141337bbda049
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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