2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran → 5-Amino-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran

HRID 234251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234251
[CH3:1][C:2]1([CH3:23])[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]2[C:13]([CH3:22])=[C:14]([N+:19]([O-])=O)[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]=2[O:3]1>C(O)C.[C].[Pd]>[NH2:19][C:14]1[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]2[O:3][C:2]([CH3:23])([CH3:1])[CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]=2[C:13]=1[CH3:22]

Komponenten

4

Edukt 1

HCID 106628262,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran

Produkt 1

HCID 105407985-Amino-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuranAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran (2.0 g, 6.4 mmol) was dissolved in ethanol (15 ml) and the solution was subjected to catalytic reduction using 5% palladium carbon (2.0 g) as a catalyst. After the catalyst was filtered off, the filtrate was concentrated. The residue was purified by column chromatography on silica gel (isopropyl ether) and then crystallized from hexane to obtain the desired compound (1.33 g, yield: 73.6%), m.p. 131°-132° C.

Aufarbeitung

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (isopropyl ether)
  4. customcrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-25f3ae4eb8ef4b8bb3714202cb4a2c20
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594154

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