Furan → Methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonate

HRID 1748917Notes

Reaction equation

HRID 1748917 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH:6]([S:8]([O:11][CH3:12])(=[O:10])=[O:9])=[CH2:7]>[I-].[Zn+2].[I-]>[CH:5]12[O:1][CH:2]([CH:6]([S:8]([O:11][CH3:12])(=[O:10])=[O:9])[CH2:7]1)[CH:3]=[CH:4]2

Participants

4

Procedure

To a four-necked flask having a capacity of 300 mL and equipped with a stirrer, a dropping funnel, and a thermometer, 150 g (2.20 mol) of furan and 15.0 g of zinc iodide were added, and 41.5 g (0.34 mol) of methyl vinylsulfonate was added to the flask from the dropping funnel at 25 to 27° C. The resultant mixture was continuously stirred at the same temperature for 2 days, and then the resultant reaction mixture was transferred to a 1 L separatory funnel. The reaction mixture was washed twice with 300 mL of water, and then unreacted furan was removed through evaporation under reduced pressure, to thereby obtain 22.0 g of methyl 7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonate.

Workup

  1. customTo a four-necked flask having
  2. customa capacity of 300 mL and equipped with a stirrer, a dropping funnel
  3. customthe resultant reaction mixture
  4. customwas transferred to a 1 L separatory funnel
  5. washThe reaction mixture was washed twice with 300 mL of water
  6. customunreacted furan was removed through evaporation under reduced pressure

Sources & evidence

ORD record
ord-5c6842535dbd474da14598b2e3430178
Source dataset
uspto-grants-2015_10
Patent number
US09152042B2

Reaction notes

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