Ethylene glycol monoallyl ether → Allyl methanesulfonylethyl ether

HRID 2269873Notes

Reaction equation

HRID 2269873 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 in vacuo 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 in vacuo

Sources & evidence

ORD record
ord-1a9ad61596ad45c384c1f6acba422e31
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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