Triphenylphosphine → 2-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxybenzyl)oxy]benzyloxy]tetralin

HRID 1242879

Reaktionsgleichung

Reaktionsgleichung von HRID 1242879
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][N:14]([CH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:27])[CH:23]=2)[CH2:18]1)[CH3:15].[CH3:28][O:29][C:30]1[CH:45]=[CH:44][C:33]([CH2:34][O:35][C:36]2[CH:43]=[CH:42][C:39]([CH2:40]O)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:15][N:14]([CH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH2:40][C:39]3[CH:42]=[CH:43][C:36]([O:35][CH2:34][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:45][CH:44]=4)=[CH:37][CH:38]=3)[CH:23]=2)[CH2:18]1)[CH3:13]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 126484214-[(4-Methoxyphenyl)methoxy]benzenemethanolHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralin

Produkt 1

HCID 219400532-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxybenzyl)oxy]benzyloxy]tetralinAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (40% toluene solution, 1.91 g) was added dropwise to THF solution (6 ml) of 2-[(N,N-dimethylamino)methyl]-6-hydroxytetralin (300 mg), 4-[(4-methoxybenzyl)oxy]benzylalcohol (1.07 g) and triphenylphosphine (1.15 g) at room temperature, which was stirred for 12 hours. The reaction mixture was concentrated, and the residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=10:1), and recrystallized (ethyl acetate-hexane) to give the titled compound (260 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified
  3. customrecrystallized (ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-037b1f8e563c4a369842696cc76cff45
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115750B1

Verknüpfte Notizen

Wird geladen…