Ethyl vinyl ether → 4,5-(Dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenenitrile

HRID 1741956Notes

Reaction equation

HRID 1741956 reaction equation
[CH3:1][C:2]1([CH3:14])[O:13][CH:10]([CH:11]=[CH2:12])[CH:4]([CH:5]([OH:9])[CH2:6][C:7]#[N:8])[O:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH:32]([O:34][CH2:35][CH3:36])=[CH2:33].[Na].[H][H]>C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[O:13][CH:10]([CH:11]=[CH2:12])[CH:4]([CH:5]([O:9][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])[CH2:6][C:7]#[N:8])[O:3]1

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 190109954,5-(Dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrileHCID 178506446HCID 178506446, compound

Product 1

HCID 190110314,5-(Dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenenitrileYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,5-(Dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile (3.54 g) was dissolved in 50 ml of methylene chloride under a nitrogen atmosphere, and a catalytic amount of pyridinium p-toluenesulfonate was added under ice cooling, followed by adding dropwise 2.57 ml of ethyl vinyl ether. After stirring for 2 hours, the reaction mixture was poured into a saturated sodium hydrogen aqueous solution, and extracted with diethyl ether. The organic layer was washed with a saturated sodium chloride aqueous solution. The obtained organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to provide 4.41 g of 4,5-(dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenenitrile having the following properties (yield 91%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f73c65576805490d954d75c2db87f74a
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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