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

HRID 2237456Notes

Reaction equation

HRID 2237456 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:8]=[CH:7][O:6][C:5]=1[CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][CH2:3][C:4]1[CH:8]=[CH:7][O:6][C:5]=1[CH2:9][CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])(=[O:22])=[O:21]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step d.) (3.58 g, 22.9 mmol) in CH2Cl2 (114 ml), was cooled to 0° C., and treated with triethylamine (9.56 ml, 68.7 mmol) followed by dropwise addition of methanesulfonyl chloride (3.88 ml, 50.4 mmol) over 10 minutes. After 1 hour, the reaction mixture was transferred to a separatory funnel and extracted with ice water (1×50 ml), 10% citric acid (2×50 ml), sat. NaHCO3 (2×50 ml) and brine (1×50 ml). The organic layer was dried (MgSO4), concentrated to 20 ml, diluted with dry dioxane (42 ml) and further concentrated to remove remaining CH2Cl2. The resulting dioxane solution of the bismesylate was immediately carried into step f)

Workup

  1. customthe reaction mixture was transferred to a separatory funnel
  2. extractionextracted with ice water (1×50 ml), 10% citric acid (2×50 ml), sat. NaHCO3 (2×50 ml) and brine (1×50 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated to 20 ml
  5. additiondiluted with dry dioxane (42 ml)
  6. concentrationfurther concentrated
  7. customto remove

Sources & evidence

ORD record
ord-3c15df1e83474b7993a68d122d0b7072
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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