Dichloromethane → HCID 19047584, compound

HRID 742454Notes

Reaction equation

HRID 742454 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6](=O)[CH2:7]C)=[CH:2]1.[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH2:16](Cl)Cl>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([O:13][CH2:10][CH3:16])=[CH2:7])=[CH:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 150538531-(3-Furanyl)-1-propanone

Product 1

HCID 19047584HCID 19047584, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

To a stirring mixture of 1-(3-furyl)-1-propanone (6.75 g, 0.0612 mol) in 150 mL of methylene chloride was added TEOF (13.2 mL, 0.079 mol) with stirring followed by 100 mg of p-toluenesulfonic acid monohydrate and the resulting mixture was stirred for 126 h. Potassium carbonate (2 g) was added to the above reaction mixture, stirred for 10 min, filtered, and concentrated in vacuo. The residue was distilled (35 mm, 82°-85° C.) to afford 2.5 g (29%) of 1-(3-furyl)-1-ethoxy-ethylene (Formula III: R3 =R4 =H; R5 =CH3CH2O; R6 =3-furanyl), as a clear oil.

Workup

  1. additionwas added TEOF (13.2 mL, 0.079 mol)
  2. stirringthe resulting mixture was stirred for 126 h
  3. stirringstirred for 10 min
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was distilled (35 mm, 82°-85° C.)

Sources & evidence

ORD record
ord-751fad5a61b14a0b9cac4ddde9d5ef36
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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