9-Acetylanthracene → N-octyl-beta-oxo-9-anthracenepropanamide

HRID 1198048

Reaktionsgleichung

[C:1]([C:4]1[C:5]2[C:10]([CH:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:3])[CH3:2].[CH2:18]([N:26]=[C:27]=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C([N-]C(C)C)(C)C.[Li+]>>[CH2:18]([NH:26][C:27](=[O:28])[CH2:2][C:1](=[O:3])[C:4]1[C:17]2[C:12]([CH:11]=[C:10]3[C:5]=1[CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

Edukt 3

HCID 699119-Acetylanthracene

HCID 76616Octyl isocyanate

HCID 2724682Lithium diisopropylamide

Produkt 1

HCID 54127851N-octyl-beta-oxo-9-anthracenepropanamide

Versuchsvorschrift

The title compound, mp 70°-72° C., was prepared from 9-acetylanthracene (5.0 g, 0.022 mol), octyl isocyanate (3.52 g, 0.022 mol), and lithium diisopropylamide (0.032 mol) using the procedure described in Example 1. Purification by flash chromatography (silica gel, 5% EtOAc/hexane) yielded 3.84 g (0.010 mol, 45.2%) of the desired product.

Quellen und Nachweise

ORD-Eintrag: ord-8740323203a848bb8eac714a022d6c3d
Quelldatensatz: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05278326

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