Water → HCID 6430550, Verbindung

HRID 1010515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010515
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[O:13].O>C1COCC1>[CH3:16][CH:2]([CH2:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[O:13])[CH3:1]

Komponenten

4

Edukt 2

HCID 962WaterHCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

Produkt 1

HCID 6430550HCID 6430550, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 0.53 g of 2 in 150 mL of dry THF in a round-bottom flask equipped with a water-cooled condenser was added a solid mixture of 31.04 g of NiCl2.6H2O and 4.27 g of Al powder (caution: exothermic). The reaction mixture was stirred at room temperature for 6 h. The solid mass was removed by filtration, and the solvent was dried over MgSO4 and removed by rotary evaporation, which afforded 0.50 g of racemic 3, predominantly the (E)-isomer. 1H NMR δ (ppm) 9.8 (t, CHO), 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 2.3 (m, CH2C(CH3)═CH), 2.2-2.4 (qd, CH2CHO), 2.0 (m, C═CHCH2CH2C(CH3)═CHCH2), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3), 1.2-1.5 (m, CH2CH(CH3)CH2CO), 0.9 (d, CH2C(CH3)═CH).

Aufarbeitung

  1. temperaturecooled condenser
  2. additionwas added
  3. customThe solid mass was removed by filtration
  4. dry with materialthe solvent was dried over MgSO4
  5. customremoved by rotary evaporation, which
  6. customafforded 0.50 g of racemic 3

Quellen und Nachweise

ORD-Eintrag
ord-ce2d9b09433745d6b36e00064bcdf3a0
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977315B2

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