Dichloromethane → 2,3-Di(2-methanesulfonyloxyethyl)furan

HRID 1518541Notes

Reaction equation

HRID 1518541 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[O:5][CH:6]=[CH:7][C:8]=1[CH2:9][CH2:10][OH:11].C(Cl)Cl.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>>[CH3:22][S:23]([O:1][CH2:2][CH2:3][C:4]1[O:5][CH:6]=[CH:7][C:8]=1[CH2:9][CH2:10][O:11][S:23]([CH3:22])(=[O:25])=[O:24])(=[O:25])=[O:24]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 196002572,3-Di(2-hydroxyethyl)furan

Product 1

HCID 866023872,3-Di(2-methanesulfonyloxyethyl)furan

Procedure

A solution of 2,3-di(2-hydroxyethyl)furan (23 mmol) in methylene chloride (114 mmol) is cooled to 0° C. and treated with triethylamine (69 mmol) followed by dropwise addition of methanesulfonyl chloride (50.4 mmol) over 10 minutes. After 1 hour the reaction mixture is transferred to a reparatory funnel and extracted with cold water, 10% citric acid, saturated aqueous NaHCO3, and brine. The organic layer is dried and concentrated twice with the aid of dioxane to produce 2,3-di(2-methanesulfonyloxy-ethyl)furan, which is used crude without further purification.

Workup

  1. extractionextracted with cold water, 10% citric acid, saturated aqueous NaHCO3, and brine
  2. customThe organic layer is dried
  3. concentrationconcentrated twice with the aid of dioxane

Sources & evidence

ORD record
ord-30a88c951e5d4b0891064e6a8befcd59
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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