Ethylene glycol monoallyl ether → Allyl methanesulfonylethyl ether

HRID 609787

Reaction equation

HRID 609787 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][CH:6]=[CH2:7].C(N(C(C)C)CC)(C)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([CH2:2][CH2:3][O:4][CH2:5][CH:6]=[CH2:7])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8116Ethylene glycol monoallyl etherHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 57200585Allyl methanesulfonylethyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine allyl hydroxyethyl ether (1.02 g, 10 mmol), and diisopropylethylamine (4.0 mL, 23 mmol), and dichloromethane (20 mL). Cool in an ice-bath. Add dropwise, methanesulfonyl chloride (1.0 mL, 13 mmol). After 1.5 hours, extract the reaction mixture with 1 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate invacuo to obtain allyl methanesulfonylethyl ether: Rf =0.80 (silica gel, 20% ethyl acetate/dichloromethane).

Workup

  1. temperatureCool in an ice-bath
  2. additionAdd dropwise
  3. extractionextract the reaction mixture with 1 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate invacuo

Sources & evidence

ORD record
ord-49773dd96dc142c1980df3ce4dd043d7
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Linked notes

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