Tetraethylene Glycol → 11-{(methylsulfonyl)oxy}-3,6,9-trioxaundecanol

HRID 1441888Notes

Reaction equation

HRID 1441888 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].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>ClCCl.[Ag]=O>[CH3:14][S:15]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])(=[O:17])=[O:16]

Participants

5

Reactant 2

HCID 8200Tetraethylene GlycolHCID 31297Methanesulfonyl chloride

Product 1

HCID 436737311-{(methylsulfonyl)oxy}-3,6,9-trioxaundecanolYield 68.5%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

250 mL of dichloromethane was added to 25 g of tetraethylene glycol and 32.8 g of silver oxide, and then a solution of 17.7 g of methanesulfonyl chloride in 50 ml of dichloromethane was added dropwise. After stirring the reaction solution at room temperature for 2 days, the solution was filtered with a celite, and then the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain 24 g of the objective compound.

Workup

  1. filtrationthe solution was filtered with a celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-cd8c2c0b99ff4922a03f0293e7cbb1e6
Source dataset
uspto-grants-2010_02
Patent number
US07655768B2

Reaction notes

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