Hydrochloric Acid → Ethyl 4-(2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy)-3-oxobutanoate

HRID 1589650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589650
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].Cl[CH2:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>O1CCCC1.C(OCC)(=O)C>[C:10]1(=[O:11])[N:6]([CH2:5][CH2:4][O:3][CH2:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]12

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 77499N-(2-Hydroxyethyl)phthalimide

Produkt 1

HCID 9840027Ethyl 4-(2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy)-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10° while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10° a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.

Aufarbeitung

  1. additionwas added
  2. additionwas added (750 ml)
  3. washThe aqueous layer was washed with ethyl acetate (300 ml)
  4. washAfter washing with water (300 ml)
  5. customthe ethyl acetate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-658154fa1ace4f51a6d9abc0526a98ae
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04572909

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