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N-Hydroxyphthalimide → 2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

HRID 29159
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 29159
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1CCN2C(=NCCC2)CC1.[CH:24]1([CH2:30]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C=O)C>[CH:24]1([CH2:30][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137636Cyclohexane, (bromomethyl)-

Produkt 1

HCID 140744162-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (27.6 mmol, 4.13 mL) was injected followed by cyclohexylmethyl bromide (23.0 mmol, 3.21 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, the reaction was cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was removed under vacuum, and the crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid. H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 3.98 (2H,d), 2.03-1.65 (5H,m), 1.31-1.03 (6H,m).

Aufarbeitung

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated to a red oil
  3. customThe reaction was partitioned between ethyl acetate and 1N HCl
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under vacuum
  7. customthe crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid

Quellen und Nachweise

ORD-Eintrag
ord-1f7bcc198d744108926d6cefdbfb57d4
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07419967B2

Notizen zur Reaktion

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