3a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione → Isoindole

HRID 1056629노트

반응식

HRID 1056629 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1(=O)[NH:11][C:10](=O)[CH:9]2[CH2:13][CH2:14][CH:15]=[CH:16][CH:8]12>C1COCC1>[CH:10]1[NH:11][CH:7]=[C:8]2[C:9]=1[CH:13]=[CH:14][CH:15]=[CH:16]2

참가 물질

4

반응물 2

HCID 152779823a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dioneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 3013853Isoindole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a suspension of LAH (22.80 g, 600 mmol) in THF (600 mL) at 0° C. was added tetrahydrophthalimide (39.45 g, 260.9 mmol) portionwise. After addition, the reaction mixture was stirred at 60° C. for 18 h, then cooled down to 0° C. and quenched carefully with water (25 mL), followed by 15% KOH aqueous solution (25 mL) and another 75 mL of water. The resulting mixture was stirred at rt for 1 h and filtered through a pad of Celite, then washed with DCM (500 mL). The filtrate was concentrated in vacuo to give isoindole as yellow oil, which was used in the next step without purification.

후처리

  1. additionAfter addition
  2. temperaturecooled down to 0° C.
  3. customquenched carefully with water (25 mL)
  4. stirringThe resulting mixture was stirred at rt for 1 h
  5. filtrationfiltered through a pad of Celite
  6. washwashed with DCM (500 mL)
  7. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-3b00c10b74d0495f8bef468d0c98ef0d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399637B2

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