2-Methyl-5-nitro-2-pentene → Methyl 3,7-dimethyl-4-nitro-6-octenoate

HRID 1447531

Reaktionsgleichung

Reaktionsgleichung von HRID 1447531
CC12CCCCN1C=CCNC2.[CH3:13][C:14](=[CH:16][CH2:17][CH2:18][N+:19]([O-:21])=[O:20])[CH3:15].[C:22]([O:27][CH3:28])(=[O:26])/[CH:23]=[CH:24]/[CH3:25]>CO>[CH3:25][CH:24]([CH:18]([N+:19]([O-:21])=[O:20])[CH2:17][CH:16]=[C:14]([CH3:15])[CH3:13])[CH2:23][C:22]([O:27][CH3:28])=[O:26]

Komponenten

5

Edukt 3

HCID 5346332-Methyl-5-nitro-2-penteneHCID 638132Methyl CrotonateHCID 20384084HCID 20384084, Verbindung

Produkt 1

HCID 23341447Methyl 3,7-dimethyl-4-nitro-6-octenoateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Methyl 3,7-Diazabicyclo[5,4,0]undec-5-ene (4 ml) is added to a solution of 2-methyl-5-nitro-2-pentene (25.0 g, 0.193 m) in methanol (200 ml). The resulting mixture is heated to 60° and methyl crotonate (30.85 g, 0.308 m) is added under nitrogen. The mixture is then stirred for 6 days at 60° after which it is cooled to room temperature and most of the methanol is removed in vacuo. The residue is treated with ether (500 ml) and washed with 2 N HCl (250 ml) and water (250 ml). The organic layer is dried (Na2SO4) and evaporated in vacuo to give 42.5 g of crude product. The crude product is purified by column chromatography on silica gel (500 g, ethyl acetate/hexane 2:98) to give methyl 3,7-dimethyl-4-nitro-6-octenoate (8.65 g, 42%).

Aufarbeitung

  1. temperatureThe resulting mixture is heated to 60°
  2. customis removed in vacuo
  3. additionThe residue is treated with ether (500 ml)
  4. washwashed with 2 N HCl (250 ml) and water (250 ml)
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customevaporated in vacuo
  7. customto give 42.5 g of crude product
  8. customThe crude product is purified by column chromatography on silica gel (500 g, ethyl acetate/hexane 2:98)

Quellen und Nachweise

ORD-Eintrag
ord-a5c2699945e04fde97f7c56979c22d81
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04177194

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