Dichloromethane → 2-(Methylsulfonyl)ethyl methanesulfonate

HRID 637059Notes

Reaction equation

HRID 637059 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][OH:7])(=[O:4])=[O:3].ClCCl.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)C(C)C)(C)C>O>[S:12]([O:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:14])(=[O:13])[CH3:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 848342-(Methylsulfonyl)ethanol

Product 1

HCID 184645972-(Methylsulfonyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 2-methylsulfonylethanol (7.7 g, 62 mmol) and dichloromethane (50 mL). Cool in an ice bath. Add methanesulfonyl chloride (7.81 g , 68.2 mmol). Add N,N-diisopropylethylamine (8.0 g, 62 mmol). After the addition of N,N-diisopropylethylamine, warm to ambient temperature. After 12 hours, add water and separate the layers. Extract the organic layer and extract with a saturated aqueous sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter and evaporate in vacuo to give the title compound: mp; 55-57° C.

Workup

  1. temperatureCool in an ice bath
  2. customseparate the layers
  3. extractionExtract the organic layer
  4. extractionextract with a saturated aqueous sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-603f9c4a10a942f38dff287e78c1a030
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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