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

HRID 915678

反応式

HRID 915678 の反応式
[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]

参加物

6

反応物 2

HCID 6570Methyl vinyl ketoneHCID 6809Phthalimide

生成物 1

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

試薬・触媒・溶媒 3

HCID 2723922Sodium ethoxide触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f3f7e03491cd406c93b57d3713e6b709
出典データセット
uspto-grants-2007_09
特許番号
US07265246B2

関連ノート

読み込み中…