Triethylamine → 2-(Methylsulfonyl)ethyl methanesulfonate

HRID 1623308Notes

Reaction equation

HRID 1623308 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][OH:7])(=[O:4])=[O:3].C(N(CC)CC)C.[S:15](Cl)([CH3:18])(=[O:17])=[O:16]>C(Cl)Cl>[CH3:18][S:15]([O:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 848342-(Methylsulfonyl)ethanol

Product 1

HCID 184645972-(Methylsulfonyl)ethyl methanesulfonateYield 7,606.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round-bottom flask containing 2-(methylsulfonyl)ethanol (400 mg, 3.22 mmol) at 0° C. was added DCM (10 ml) and triethylamine (4.91 μl, 0.035 mmol), followed by dropwise addition of mesyl chloride (2.96 mg, 0.026 mmol). The ice bath was removed and the reaction mixture was stirred at ambient temperature for 2 hr. The reaction mixture was diluted with DCM and washed with sat NaHCO3 and then sat NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting residue was purified via ISCO (0-60% EtOAc/Hexane) to yield 2-(methylsulfonyl)ethyl methanesulfonate (400 mg, 61%). LCMS (m/z): 203.0 (MH+), retention time=0.37 min.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with DCM
  3. washwashed
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified via ISCO (0-60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-1f30a8ddda46400e8efcfaa2580fb787
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

Loading…