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

HRID 1755495Notes

Reaction equation

HRID 1755495 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

Reactant 2

HCID 8029FuranHCID 12260019methyl vinylsulfonate

Product 1

HCID 20768638Methyl 7-oxabicyclo[2.2.1]hept-5-ene-2-sulfonateYield 34%

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

A four-neck flask having an internal capacity of 300 mL and fitted with a stirrer, a dropping funnel and a thermometer was charged with 150 g (2.20 mol) of furan and 15.0 g of zinc iodide, and 41.5 g (0.34 mol) of methyl vinylsulfonate was added dropwise from the dropping funnel at a temperature of 25 to 27° C. Stirring was continued at the same temperature for two days, and the reaction mixture was then transferred to a 1 L separating funnel. Following washing twice with 300 mL samples of water, the unreacted furan was removed by distillation under reduced pressure, yielding 22.0 g of methyl 7-oxabicyclo[2.2.1]hept-2-ene-5-sulfonate.

Workup

  1. customA four-neck flask having
  2. customan internal capacity of 300 mL and fitted with a stirrer, a dropping funnel
  3. additionwas added dropwise from the dropping funnel at a temperature of 25 to 27° C
  4. customseparating funnel
  5. washFollowing washing twice with 300 mL samples of water
  6. customthe unreacted furan was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-d0423087a2cb4bbeaa561a3bf29ad693
Source dataset
uspto-grants-2015_10
Patent number
US09170487B2

Reaction notes

Loading…