1,5-Diazabicyclo(5,4,0)undec-5-ene → Methyl 3,7-dimethyl-4-nitro-6-octenoate

HRID 27647

Reaktionsgleichung

Reaktionsgleichung von HRID 27647
N12CCCCC1C=NCCC2.[CH3:12][C:13](=[CH:15][CH2:16][CH2:17][N+:18]([O-:20])=[O:19])[CH3:14].[C:21]([O:26][CH3:27])(=[O:25])/[CH:22]=[CH:23]/[CH3:24]>CO>[CH3:24][CH:23]([CH:17]([N+:18]([O-:20])=[O:19])[CH2:16][CH:15]=[C:13]([CH3:14])[CH3:12])[CH2:22][C:21]([O:26][CH3:27])=[O:25]

Komponenten

5

Edukt 3

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 5346332-Methyl-5-nitro-2-penteneHCID 638132Methyl Crotonate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

1,5-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-1631e3596e704285b82a8058350af411
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04222937

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