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

HRID 1848667Notes

Reaction equation

HRID 1848667 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-c100fb27d90e449e99ed1970a55ab6c0
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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