Toluene → Oxolan-3-ylmethanesulfonyl chloride

HRID 397648Notes

Reaction equation

HRID 397648 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][S:7]([O-:10])(=O)=[O:8])[CH2:2]1.[Na+].C1(C)C=CC=CC=1.S(Cl)([Cl:21])=O>CN(C)C=O>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][S:7]([Cl:21])(=[O:10])=[O:8])[CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 23670188Sodium tetrahydrofuran-3-ylmethanesulfonate

Product 1

HCID 23000703Oxolan-3-ylmethanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium tetrahydrofuran-3-ylmethanesulfonate (1.0 g) [see Preparation 10] was dissolved in dimethylformamide (0.05m)) and thionyl chloride (5.3 ml) was added. The reaction mixture was heated under reflux for 5 hours, cooled and toluene (10 ml) added. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer was separated, washed with brine, dried over magnesium sulphate and the solvent removed under reduced pressure to afford tetrahydrofuran-3-ylmethanesulfonyl chloride (0.22 g) as a yellow oil. 1H-NMR (CDCl3) δ: 3.95 (1H, m), 3.90-3.60 (2H, m), 3.45 (1H, m), 3.00 (2H, m), 2.30 (1H, m), 2.10 (1H, m), 1.80 (1H, m).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 5 hours
  4. temperaturecooled
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was partitioned between ethyl acetate and water
  7. customthe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3a9898670e6c4df1a5970751148532ad
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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