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

HRID 2070562ノート

反応式

HRID 2070562 の反応式
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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178418797HCID 178418797、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2fe247b6b8064819af340b05c2d03f6c
出典データセット
uspto-grants-2012_10
特許番号
US08299296B2

反応ノート

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