Methanesulfonyl chloride → 2-(Methylsulfonyl)ethyl methanesulfonate

HRID 627025Notes

Reaction equation

HRID 627025 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][OH:7])(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([O:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 848342-(Methylsulfonyl)ethanol

Product 1

HCID 184645972-(Methylsulfonyl)ethyl methanesulfonateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask, 2-(methylsulfonyl)ethanol (1.24 g, 9.99 mmol, Eq: 1.00) was combined with DCM (5 mL). To the resulting solution was added diisopropylethylamine (2.1 mL, 12.0 mmol, Eq: 1.2) and methanesulfonyl chloride (1.37 g, 931 μL, 12.0 mmol, Eq: 1.2). The ice bath was removed and the reaction was stirred at rt overnight. The crude reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 80 g, 10% to 80% EtOAc in hexanes) to give 2-(methylsulfonyl)ethyl methanesulfonate (1.01 g).

Workup

  1. customThe ice bath was removed
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 80 g, 10% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-59af46faaf0f486bb3881a064cbe3f58
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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