1,4-Butanediol → 1,4-Bis[1-(t-butylazo)-1,3-dimethylbutoxy]butane

HRID 1578575

反応式

HRID 1578575 の反応式
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH2:5][CH2:6][OH:7].[H][H].[C:11]([N:15]=[N:16][C:17](Cl)([CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:18])([CH3:14])([CH3:13])[CH3:12]>O1CCOCC1>[C:11]([N:15]=[N:16][C:17]([CH3:18])([O:7][CH2:6][CH2:5][CH2:4][CH2:3][O:8][C:17]([CH3:18])([N:16]=[N:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:19][CH:20]([CH3:22])[CH3:21])([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 80641,4-ButanediolHCID 24758Sodium hydrideHCID 23344796(E)-1-tert-Butyl-2-(2-chloro-4-methylpentan-2-yl)diazene2 回HCID 178418361HCID 178418361、化合物

生成物 1

HCID 214297711,4-Bis[1-(t-butylazo)-1,3-dimethylbutoxy]butane収率 93%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a slurry of 1.98 grams (.047 moles) of sodium hydride in 50 ml. dioxane in a 100 ml. reaction flask equipped with a magnetic stirrer, thermometer, addition funnel, and gas bubbler, was added 2.11 grams (.0235 moles) of 1,4-butanediol. The reaction was followed by hydrogen evolution and it required over 8 hours to complete so the reaction was stirred overnight. The next morning, 9.59 grams (.047 moles) of 2-t-butylazo-2-chloro-4-methylpentane was added dropwise at room temperature to the stirred salt solution. After the addition was complete, the reaction was stirred 4 hours and then checked by gas chromatography. Gas chromatography indicated there was a small amount of unreacted 2-t-butylazo-2-chloro-4-methylpentane left so the reaction was allowed to stir overnight. The next day, the reaction mixture was poured into 200 mls. of cold water and extracted with pentane. The pentane solution was washed with H2O, dried over anhydrous sodium sulfate, filtered and the pentane evaporated to leave 9.3 grams (93% yield) of a straw yellow liquid. The crude product was purified by column chromatography over alumina, using pentane as the eluent. The infrared spectrum of the purified material was in agreement with the structure of the desired product.

後処理

  1. customreaction flask
  2. customequipped with a magnetic stirrer
  3. additionthermometer, addition funnel
  4. additionAfter the addition
  5. stirringthe reaction was stirred 4 hours
  6. waitleft so the reaction
  7. stirringto stir overnight
  8. additionThe next day, the reaction mixture was poured into 200 mls
  9. extractionof cold water and extracted with pentane
  10. washThe pentane solution was washed with H2O
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customthe pentane evaporated

出典と根拠

ORDレコード
ord-a540485c68884e1cbe9ef37091c1029d
出典データセット
uspto-grants-1976_02
特許番号
US03937761

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