Dimethylformamide → 2,5-dimethylfuran-3-sulfonyl Chloride

HRID 1899734Notes

Reaction equation

HRID 1899734 reaction equation
CN(C=O)C.[S:6]([Cl:10])(Cl)(=[O:8])=[O:7].[CH3:11][C:12]1[O:13][C:14]([CH3:17])=[CH:15][CH:16]=1>CCOC(C)=O.CCCCCC>[CH3:11][C:12]1[O:13][C:14]([CH3:17])=[CH:15][C:16]=1[S:6]([Cl:10])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 122662,5-DimethylfuranHCID 24648Sulfuryl chloride

Product 1

HCID 27950242,5-dimethylfuran-3-sulfonyl ChlorideYield 22.3%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

DMF (2.2 ml, 28 mmol) and sulfuryl chloride (1.9 ml, 24 mmol) were stirred at 0° C. for 30 minutes and then the 2,5-dimethylfuran (1.5 ml, 14 mmol) was slowly added. The reaction mixture was heated to 60° C. for 30 minutes, then cooled to ambient temperature and poured into ice water (200 ml). The aqueous layer was extracted with EtOAc (100 ml) and then the organic layer was dried (MgSO4) filtered and concentrated to collect 0.69 g of a brown liquid. Flash chromatography (5% EtOAc/hexane) provided 0.607 g (22% yield) of a yellow liquid.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionThe aqueous layer was extracted with EtOAc (100 ml)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto collect 0.69 g of a brown liquid

Sources & evidence

ORD record
ord-4708ae96d4264a71bb5335978b27695e
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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