Methanesulfonyl chloride → 2-(2-Ethyl-1,3-dioxolan-2-yl)ethyl methanesulfonate

HRID 2200571Notes

Reaction equation

HRID 2200571 reaction equation
[CH2:1]([C:3]1([CH2:8][CH2:9][OH:10])[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].[CH3:11][S:12](Cl)(=[O:14])=[O:13]>C(Cl)Cl.O>[CH3:11][S:12]([O:10][CH2:9][CH2:8][C:3]1([CH2:1][CH3:2])[O:7][CH2:6][CH2:5][O:4]1)(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 139403682-(2-Ethyl-1,3-dioxolan-2-yl)ethan-1-ol

Product 1

HCID 888956262-(2-Ethyl-1,3-dioxolan-2-yl)ethyl methanesulfonateYield 140.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-ethyl-1,3-dioxolan-2-yl)ethanol (233 mg, 1.59 mmol) and TEA (327 mg, 3.2 mmol) in DCM (10 mL) was added methanesulfonyl chloride (0.23 ml, 2.92 mmol) at 0° C. The resulting mixture was stirred at room temperature for 3 h. The mixture was diluted with DCM and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 2-(2-ethyl-1,3-dioxolan-2-yl)ethyl methanesulfonate (500 mg, 100%) as yellow oil that was used without purification. Product tlc [DCM/methanol (100:1) developed with potassium permanganate, Rf 0.6]

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56c32ec957044d3b8751658b7d1958dd
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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