Methanesulfonyl chloride → 2-Methanesulfonyloxyethyl 2,2,2-trifluorethyl ether

HRID 637200Notes

Reaction equation

HRID 637200 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][O:4][CH2:5][CH2:6][OH:7].C(N(CC)C(C)C)(C)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[F:1][C:2]([F:9])([F:8])[CH2:3][O:4][CH2:5][CH2:6][O:7][S:20]([CH3:19])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-ol

Product 1

HCID 186737182-Methanesulfonyloxyethyl 2,2,2-trifluorethyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 2-hydroxyethyl 2,2,2-trifluoroethyl ether (0.5 mmol) and N,N-diisopropylethylamine (1 mmol) in dichloromethane (20 mL). Cool in a ice-bath. Add dropwise, methanesulfonyl chloride (0.6 mmol). After 2 hours, extract with 1 M hydrochloric acid solution and 5% sodium bicarbonate solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give 2-methanesulfonyloxyethyl 2,2,2-trifluoroethyl ether.

Workup

  1. temperatureCool in a ice-bath
  2. additionAdd dropwise
  3. extractionextract with 1 M hydrochloric acid solution and 5% sodium bicarbonate solution
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-5517df197fcd4174a16f532a3c57899d
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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