Methanesulfonyl chloride → Fur-2-ylmethyl 2-methanesulfonylethyl ether

HRID 1584452Notes

Reaction equation

HRID 1584452 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][C:6]1[O:7][CH:8]=[CH:9][CH:10]=1.C(N(CC)C(C)C)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH3:20][S:21]([CH2:2][CH2:3][O:4][CH2:5][C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10103270Fur-2-ylmethyl 2-hydroxyethyl ether

Product 1

HCID 21223641Fur-2-ylmethyl 2-methanesulfonylethyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine fur-2-ylmethyl 2-hydroxyethyl ether (10 mmol), and N,N-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 fur-2-ylmethyl 2-methanesulfonylethyl ether.

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-fa3ebdede7aa4ffebd39c1c38da4f227
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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