Tetraethylene Glycol → 1,11-Bis(methanesulfonyloxy)-3,6,9-trioxandecane

HRID 1441890Notes

Reaction equation

HRID 1441890 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][O:13][S:22]([CH3:21])(=[O:24])=[O:23])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8200Tetraethylene GlycolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 36378751,11-Bis(methanesulfonyloxy)-3,6,9-trioxandecaneYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15 g of tetraethyleneglycol and 23.4 g of triethylamine were dissolved in 200 mL of dichloromethane, to which 22.1 g of methanesulfonylchloride was added dropwise at 0° C., and then the solution was stirred for 1 hour. The reaction solution was filtrated to remove insolubles, and then the filtrate was concentrated under reduced pressure. The residue was separated with ethyl acetate-water, and the organic layer was concentrated under reduced pressure after washing with water. The residue was purified with silica gel column chromatography to obtain 27 g of the objective compound.

Workup

  1. additionwas added dropwise at 0° C.
  2. filtrationThe reaction solution was filtrated
  3. customto remove insolubles
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was separated with ethyl acetate-water
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. washafter washing with water
  8. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-9c055947ea344fc89bbc27ee17e3b262
Source dataset
uspto-grants-2010_02
Patent number
US07655768B2

Reaction notes

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