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

HRID 1486021Notes

Reaction equation

HRID 1486021 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-2edd7dc147794b1793544171a7c6355e
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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