Water → 2,6,10-Trimethyl-13-nitrotetradeca-2,6,12-triene

HRID 1010518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010518
C(O[CH:5]([CH2:11][CH:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH:6]([N+:8]([O-:10])=[O:9])[CH3:7])(=O)C.CC(C)([O-])C.[K+].CCOCC.O>C(O)(C)(C)C>[CH3:24][CH:12]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH2:11][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH3:7]

Komponenten

6

Edukt 4

HCID 962WaterHCID 3283Diethyl EtherHCID 23665647Potassium tert-butoxideHCID 72491401HCID 72491401, Verbindung

Produkt 1

HCID 714152562,6,10-Trimethyl-13-nitrotetradeca-2,6,12-trieneAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel2×

Versuchsvorschrift

A solution of 1.30 g of 5 in 25 mL of t-butyl alcohol was added to a solution of 30 mL of t-butyl alcohol containing 0.53 g of potassium t-butoxide. The reaction mixture was stirred at room temperature for 1 h, whereupon it was added to 150 mL of ether and 20 mL of H2O. The organic layer was separated and dried over MgSO4, and the solvent was removed by rotary evaporation to afford 0.40 g of racemic RG-4, predominantly the (E)-isomer. 1H NMR δ (ppm) 7.18 (t, CH═CNO2), 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 2.19 (s, C═C(CH3)NO2), 2.0 (m, C═CHCH2CH2C(CH3)═CHCH2), 2.2-2.3 (m, CH2C═CNO2), (CH3C═(CH3), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3), 1.2-1.5 (m, CH2CH(CH3)CH2), 0.95 (d, CH2CH(CH3)CH2).

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a4de41af06ef4d7f925083e58500ec8d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977315B2

Notizen zur Reaktion

Wird geladen…