Sodium Cyanide → 4,5-(Dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile

HRID 1741951ノート

反応式

HRID 1741951 の反応式
S([O-])([O-])(=O)=O.[Mg+2].[C-:7]#[N:8].[Na+].[O:10]1[CH:12]([CH:13]2[O:19][C:18]([CH3:21])([CH3:20])[O:17][CH:14]2[CH:15]=[CH2:16])[CH2:11]1>CO>[CH3:20][C:18]1([CH3:21])[O:17][CH:14]([CH:15]=[CH2:16])[CH:13]([CH:12]([OH:10])[CH2:11][C:7]#[N:8])[O:19]1

参加物

5

反応物 3

HCID 8929Sodium CyanideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 100123231,2-Epoxy-3,4-(dimethylmethylenedioxy)-5-hexene

生成物 1

HCID 190109954,5-(Dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile収率 23.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
10 °C

実験手順

Fifty milliliters of a saturated magnesium sulfate aqueous solution were cooled to 10° C., and 10.23 g of sodium cyanide was gradually added not to proceed over 10° C. After stirring at 10° C. for 45 minutes, a solution of 7.61 g of 1,2-epoxy-3,4-(dimethylmethylenedioxy)-5-hexene in 30 ml of methanol was gradually added to the above mixture not to proceed over 10° C. After stirring at room temperature for 2 hours, the reaction mixture was extracted with ethyl acetate. The extract was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 2.11 g of 4,5-(dimethylmethylenedioxy)-3-hydroxy-6-heptenenitrile having the following properties.

後処理

  1. customto proceed over 10° C
  2. customto proceed over 10° C
  3. stirringAfter stirring at room temperature for 2 hours
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with a sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-19f527fb225e47e58d7e13763e4dfa27
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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