Water → N-(Hex-5-enyl)phthalimide

HRID 361474

反応式

HRID 361474 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K].O>CS(C)=O>[CH2:2]([N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

参加物

5

反応物 3

HCID 962WaterHCID 759066-Bromo-1-hexeneHCID 24194345Phthalimide potassium salt

生成物 1

HCID 12422290N-(Hex-5-enyl)phthalimide収率 100.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

This example illustrates a synthesis of N-(5,6-Oxidohexyl)phthalimide (inventive compound no. 1103). 1-bromo-5-hexene (6.52 g, 40 mmol) was added to a potassium phthalimide (7.4 g, 40 mmol) suspension in 50 mL of dimethyl sulfoxide and stirred overnight. After 12 hours of stirring at room temperature, the reaction was poured into a separatory funnel containing 300 mL of water and extracted with dichloromethane (5×200 mL). The organic extracts were combined, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel (eluant: 10% acetone/hexane) to yield 9.2 g (100% yield) of N-(5-Hexenyl)phthalimide (inventive compound no. 1101).

後処理

  1. stirringAfter 12 hours of stirring at room temperature
  2. additionthe reaction was poured into a separatory funnel
  3. extractionextracted with dichloromethane (5×200 mL)
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel (eluant: 10% acetone/hexane)

出典と根拠

ORDレコード
ord-99f0c994954d46a59fcb29e44f25afb9
出典データセット
uspto-grants-1999_02
特許番号
US05866576

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