Hydrochloric Acid → HCID 22286311, Verbindung

HRID 1062266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062266
[OH:1][CH2:2][CH2:3][CH2:4][O:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].Cl>ClCCl>[C:25]([Si:22]([CH3:24])([CH3:23])[O:1][CH2:2][CH2:3][CH2:4][O:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])([CH3:28])([CH3:27])[CH3:26]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 222859102-(3-Hydroxy-propoxy)-isoindole-1,3-dione

Produkt 1

HCID 22286311HCID 22286311, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-hydroxy-propoxy)-isoindole-1,3-dione (17.5 g, 79.1 mmol) and imidazole (5.92 g, 86.1 mmol) in dichloromethane (200 mL) was added tert-butyldimethylsilyl chloride (13.2 g, 86.1 mmol). After 30 min, the reaction was transferred to a separatory funnel and shaken with dilute aqueous hydrochloric acid (400 mL). The organic layer was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to afford 2-[3-(tert-Butyl-dimethyl-silanyloxy)-propoxy]-isoindole-1,3-dione (26.3 g, 99% yield) as a viscous liquid: 1H NMR (400 MHz, CDCl3) δ 7.76 (m, 2H), 7.67 (m, 2H), 4.25 (t, 2H, J=5.9 Hz), 3.77 (t, 2H, J=6.0 Hz), 1.91 (quintet, 2H, J=6.1 Hz), 0.82 (s, 9H), 0.00 (s, 6H).

Aufarbeitung

  1. customthe reaction was transferred to a separatory funnel
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0ce0678a112b4d628c42988145fd3ef1
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960614B2

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