Allyl bromide → HCID 57437443, Verbindung
Reaktionsgleichung
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]2[O:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:4][C:3]=1[CH3:15].[CH2:16](Br)[CH:17]=[CH2:18]>C1COCC1>[CH2:18]([C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]2[O:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:4][C:3]=1[CH3:15])[CH:17]=[CH2:16]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
The corresponding Grignard-reagent is prepared form 2-(4-bromo-3,5-dimethyl-phenyl)-[1,3]dioxane (2.5 g, 9.22 mmol) and Mg (258 mg, 10.6 mmol) in THF (50 mL). To this reagent allylbromide (1.23 g, 10.14 mmol) is added dropwise at rt. The reaction mixture becomes warm (40° C.) and it is stirred for 16 h. The reaction is quenched by adding water. The mixture is extracted with EA. The organic extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 10:1 to give 2-(4-allyl-3,5-dimethyl-phenyl)-[1,3]dioxane (1.8 g) as a colourless oil; LC-MS: tR=1.02 min, [M+1]+=233.22, 1H NMR (CDCl3): δ 7.12 (s, 2H), 5.94-5.80 (m, 1H), 5.44 s, 1H), 4.95 (dd, J=1.8, 10.0 Hz, 1H), 4.80 (dd, J=1.8, 17.0 Hz, 1H), 4.30-4.21 (m, 2H), 4.04-3.92 (m, 2H), 3.40-3.34 (m, 2H), 2.32-2.26 (m, 8H).