Dimethylformamide → 2,3:4,5-Di(2-butenyl)tetrahydrofurfural

HRID 73724Notes

Reaction equation

HRID 73724 reaction equation
CN1C2C(C(OC)=O)C(O[CH:11]([C:19]3[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=3)[C:12]3[CH:17]=[CH:16][C:15](F)=[CH:14]C=3)CC1CC2.[OH:30]OS([O-])=O.[K+].CN([CH:39]=[O:40])C>>[CH2:20]1[CH:19]2[CH:11]3[C:12]([CH:39]=[O:40])([O:30][CH:24]2[CH2:23][CH:22]=[CH:21]1)[CH2:17][CH:16]=[CH:15][CH2:14]3

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 18756317HCID 18756317, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 313412,3:4,5-Di(2-butenyl)tetrahydrofurfural

Procedure

To a solution of R-9 (500 mg, 2.06 mmol) and R-10 (337.6 mg, 2.06 mmol) in DMF (20 mL) is added oxone (758.5 mg, 1.23 mmol) and the solution is stirred at room temperature for 1 hour. The mixture is concentrated in vacuo and the residue is diluted in CH2Cl2 and is washed with saturated aqueous NaHCO3. The organics are dried with Na2SO4, filtered and concentrated in vacuo to give R-11 (787 mg).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionthe residue is diluted in CH2Cl2
  3. washis washed with saturated aqueous NaHCO3
  4. dry with materialThe organics are dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-114fb72fbc8d41be927019dba3cad071
Source dataset
uspto-grants-2014_09
Patent number
US08829200B2

Reaction notes

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