trans-2,cis-6-Nonadienal → 2-((4E,8Z)-undeca-2.4.8-trien-2-yl)naphthalene
Reaktionsgleichung
[Br-].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:13].[Li][CH2:34]CCC.[CH:38](=O)/[CH:39]=[CH:40]/[CH2:41][CH2:42]/[CH:43]=[CH:44]\[CH2:45]C>>[CH3:34][C:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=1)=[CH:13]/[CH:45]=[CH:44]/[CH2:43][CH2:42]/[CH:41]=[CH:40]\[CH2:39][CH3:38]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (2.40 g, 4.83 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.0 mL, 4.83 mmol, 1.0 equiv.) and (2E,6Z)-Nona-2,6-dienal (1.00 g, 7.24 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.90 g (67%) of the title compound as a a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).