3-Chlorocyclopent-1-ene → 3-(5-Methoxyheptyl)cyclopent-1-ene

HRID 569218

반응식

HRID 569218 반응식
[Mg].Cl[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([O:10][CH3:11])[CH2:8][CH3:9].Cl[CH:13]1[CH2:17][CH2:16][CH:15]=[CH:14]1.[Cl-].[NH4+]>O1CCCC1>[CH3:11][O:10][CH:7]([CH2:8][CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH:17]1[CH2:16][CH2:15][CH:14]=[CH:13]1

참가 물질

6

반응물 4

HCID 72973-Chlorocyclopent-1-eneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 139240411-Chloro-5-methoxyheptane

생성물 1

HCID 139240423-(5-Methoxyheptyl)cyclopent-1-ene수율 89.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-25 °C

실험 절차

A three-neck, round-bottomed flask containing magnesium metal turnings (7.2 g, 0.299 moles), is equipped with a Friedrich condenser and kept under a nitrogen atmosphere. Tetrahydrofuran (300 ml) is added and the contents are allowed to stir. A solution of 1-chloro-5-methoxyheptane (48.1 g, 0.292 moles) is added in small portions and refluxed. The mixture is allowed to stir for 3 hours. The resultant dark yellow solution is cooled to -25° C., and the condenser is removed and replaced with a dry ice addition funnel. A solution of 3-chlorocyclopentene (29.9 g, 0.292 moles) is added over a period of one hour. The viscous solution is poured into two liters of saturated ammonium chloride, extracted with ether, and dried over anhydrous sodium sulfate. Distillation yields 3-(5-methoxyheptyl)cyclopentene (51.5 g, 0.262 moles) as a clear, colorless oil boiling at about 90° C. at 0.3 mm and 54° C. at 0.1 mm.

후처리

  1. customis equipped with a Friedrich condenser
  2. temperaturerefluxed
  3. stirringto stir for 3 hours
  4. customthe condenser is removed
  5. additionreplaced with a dry ice addition funnel
  6. extractionextracted with ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationDistillation

출처 및 근거

ORD 기록
ord-a150cba31fd74908839148ec13952597
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731458

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