Sodium sulfite heptahydrate → Sodium tetrahydrofuran-3-ylmethanesulfonate

HRID 397647Notes

Reaction equation

HRID 397647 reaction equation
O.O.O.O.O.O.O.[S:8]([O-:11])([O-:10])=[O:9].[Na+:12].[Na+].Br[CH2:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1>O1CCOCC1.O>[O:18]1[CH2:19][CH2:20][CH:16]([CH2:15][S:8]([O-:11])(=[O:10])=[O:9])[CH2:17]1.[Na+:12]

Participants

5

Reactant 2

HCID 160916Sodium sulfite heptahydrateHCID 141734223-(Bromomethyl)oxolane

Product 1

HCID 23670188Sodium tetrahydrofuran-3-ylmethanesulfonateYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium sulfite heptahydrate (6.10 g) was added to a solution of 3-(bromomethyl)tetrahydrofuran (2.0 g) [see Preparation 9] in 1,4-dioxane (9 ml) and water (9 ml). The reaction mixture was then heated under reflux and stirred for 18 hours, cooled and the solvent removed under reduced pressure. The resulting solid was dissolved in water and concentrated to a low volume. The solid formed was then collected to afford sodium tetrahydrofuran-3-ylmethanesulfonate (1.30 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe resulting solid was dissolved in water
  6. concentrationconcentrated to a low volume
  7. customThe solid formed
  8. customwas then collected

Sources & evidence

ORD record
ord-2745747e256148b3a074e2b0bb6aa496
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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