Hydrochloric Acid → 3-(But-3-en-1-yl)cyclopent-2-en-1-one

HRID 2070562노트

반응식

HRID 2070562 반응식
C(O[C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)C.[CH2:10]([Mg]Br)[CH2:11][CH:12]=[CH2:13].Cl>O1CCCC1>[CH2:13]([C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)[CH2:12][CH:11]=[CH2:10]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178418797HCID 178418797, 화합물

생성물 1

HCID 127398563-(But-3-en-1-yl)cyclopent-2-en-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 3-ethoxycyclopent-2-enone (2.37 g) in tetrahydrofuran (30 mL) was added dropwise a 0.5M tetrahydrofuran solution of 3-butenylmagnesium bromide (38.4 mL) under nitrogen atmosphere at −78° C. over 10 minutes, followed by stirring at −78° C. for 3 hours and then at room temperature overnight. Then, after addition of 2N aqueous hydrochloric acid solution, the reaction mixture was stirred for 30 minutes and then extracted with ethyl acetate twice. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel to give 3-(3-butenyl)cyclopent-2-enone (1.1 g).

후처리

  1. customat room temperature
  2. customovernight
  3. stirringthe reaction mixture was stirred for 30 minutes
  4. extractionextracted with ethyl acetate twice
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-2fe247b6b8064819af340b05c2d03f6c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299296B2

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