Dimethylformamide → 2-[3-(2-Phenyl-1,3-dioxolan-2-yl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1013120

Reaktionsgleichung

Reaktionsgleichung von HRID 1013120
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:9][CH2:8][CH2:7][O:6]1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K].CN(C=O)C>O>[C:10]1([C:5]2([CH2:4][CH2:3][CH2:2][N:20]3[C:16](=[O:26])[C:17]4[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:19]3=[O:21])[O:9][CH2:8][CH2:7][O:6]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 128663382-(3-Chloropropyl)-2-phenyl-1,3-dioxolaneHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 574477532-[3-(2-Phenyl-1,3-dioxolan-2-yl)propyl]-1H-isoindole-1,3(2H)-dioneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Add 2-(3-chloropropyl)-2-phenyl-[1,3]dioxolane (38 g, 168 mmol) and potassium phthalimide (34.2 g, 184.4 mmol) to DMF (80 mL) and stir for 40 min at 150° C. Cool the reaction to RT, dilute with water (1 L) and extract the mixture with a mixture of EtOAc (500 mL) and hexanes (500 mL) and DCM (2 L). Dry (sodium sulfate), concentrate and recrystallize the solid from hot ethanol (600 mL). Filter and dry the residue under vacuum to isolate the title compound as a white solid (47.62 g, 84%).

Aufarbeitung

  1. temperatureCool
  2. customthe reaction to RT
  3. extractionextract the mixture
  4. additionwith a mixture of EtOAc (500 mL) and hexanes (500 mL) and DCM (2 L)
  5. dry with materialDry (sodium sulfate)
  6. concentrationconcentrate
  7. customrecrystallize the solid from hot ethanol (600 mL)
  8. filtrationFilter
  9. customdry the residue under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6e014771ee0a4e1b874404a23cd87f81
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981882B2

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