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

HRID 1056629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056629
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 3013853Isoindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3b00c10b74d0495f8bef468d0c98ef0d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399637B2

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