Triethylamine → 2-(2-Hydroxy-3,3-dimethylbutoxy)-isoindole-1,3-dione

HRID 1766823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766823
[CH3:1][C:2]([CH3:7])([CH3:6])[CH:3]1[O:5][CH2:4]1.[OH:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[OH:5][CH:3]([C:2]([CH3:7])([CH3:6])[CH3:1])[CH2:4][O:8][N:9]1[C:13](=[O:14])[C:12]2[C:11](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]1=[O:19]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 921742-tert-Butyloxirane

Produkt 1

HCID 211115332-(2-Hydroxy-3,3-dimethylbutoxy)-isoindole-1,3-dioneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 3,3-dimethyl-1,2-epoxybutane (5.0 mL, 41.0 mmol) in DMF (100 mL) was added N-hydroxyphthalimide (8.03 g, 49.2 mmol) and triethylamine (6.90 mL, 49.2 mmol). The solution was heated at 75° C. for two days. The solution was cooled to room temperature, diluted with ethyl acetate and washed with water (2×), saturated potassium carbonate (3×), brine (2×), dried over Na2SO4 and concentrated to an orange solid. Purification using flash column chromatography (dichloromethane) provided the desired product as a white solid (1.50 g, 14%).

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. washwashed with water (2×), saturated potassium carbonate (3×), brine (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to an orange solid
  5. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-51f50cf265ce474683a9368c3598e95f
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230099B2

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