2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

HRID 49709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49709
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2].[CH3:22][Mg]Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1.C(OCC)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]=[C:9]([CH3:22])[C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18188103t-Butyl 3-acetoxy-4-nitrophenylacetateHCID 178418332HCID 178418332, Verbindung2×

Produkt 1

HCID 18188096t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of t-butyl 3-acetoxy-4-nitrophenylacetate (8.0 g, Reference Example 13) in tetrahydrofuran (350 mL) at −15° C. under argon was treated dropwise with methyl magnesium chloride solution in diethyl ether (7mL, 3M) and after 2 hours a further aliquot of methyl magnesium chloride solution in diethyl ether (7 mL, 3M). After stirring for a further 1 hour the reaction mixture was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (10.4 g), then stirred at room temperature overnight, then partially evaporated and then treated with dichloromethane. The mixture was washed with water, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with dichloromethane to give the title compound (1.66 g) as a yellow oil.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. custompartially evaporated
  3. additiontreated with dichloromethane
  4. washThe mixture was washed with water
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-acffe975056b4b4b987c21ee70571b50
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706738B2

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