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

HRID 1741956ノート

反応式

HRID 1741956 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f73c65576805490d954d75c2db87f74a
出典データセット
uspto-grants-1994_08
特許番号
US05334740

反応ノート

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