Methyl vinyl ketone → 2-(3-Oxobutyl)isoindoline-1,3-dione

HRID 915678

반응식

HRID 915678 반응식
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH:12]([C:14]([CH3:16])=[O:15])=[CH2:13]>C(OCC)(=O)C.C(O)C.CC[O-].[Na+]>[O:15]=[C:14]([CH3:16])[CH2:12][CH2:13][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

참가 물질

6

반응물 2

HCID 6570Methyl vinyl ketoneHCID 6809Phthalimide

생성물 1

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dione수율 92.1%

시약·촉매·용매 3

HCID 2723922Sodium ethoxide촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

Prepare a suspension of phthalimide (5 g, 34 mmol) in ethyl acetate (40 mL). Add methyl vinyl ketone (2.8 mL, 34 mmol) followed by NaOEt (116 mg, 1.7 mmol) in ethanol (10 mL). Stir the reaction at room temperature for 2 hours, then heat to reflux and stir for 3 hours. Concentrate the reaction in vacuo to a solid. Recrystallize the solid from ethanol to afford 2-(3-oxobutyl)isoindole-1,3-dione (6.8 g). 1H NMR (CDCl3) δ 7.82-7.88 (m, 2H), 7.69-7.77 (m, 2H), 3.97 (t, J=7 Hz, 2H), 2.88 (t, J=7 Hz, 2H), 2.20 (s, 3H).

후처리

  1. customPrepare
  2. customthe reaction at room temperature for 2 hours
  3. temperatureheat
  4. temperatureto reflux
  5. stirringstir for 3 hours
  6. concentrationConcentrate
  7. customthe reaction in vacuo to a solid
  8. customRecrystallize the solid from ethanol

출처 및 근거

ORD 기록
ord-f3f7e03491cd406c93b57d3713e6b709
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265246B2

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