[CH:1]1([C:7](=[CH2:10])[CH:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:11]([Mg]Br)=[CH:12][CH2:13][CH3:14].BrCCC=C.[Mg]>CCOCC>[CH:1]1([C:7]([CH:8]([OH:9])[CH2:14][CH2:13][CH:12]=[CH2:11])=[CH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
2-Cyclohexylprop-2-en-1-al (69 g, 0.5 mol) in 100 ml of ether was slowly added to but-1-enylmagnesium bromide prepared by slow addition of 4-bromo-but-1-ene (81.0 g, 0.6 mol) in 100 ml of ether at 0° C. to magnesium turnings (13.2 g, 0.55 mol) in 300 ml of ether. After the addition was complete, the reaction mixture was allowed to warm to room temperature (RT) and was stirred for additional 3 hours. After quenching with 2N HCl, the organic phase was separated, washed with H2O until neutral pH was achieved, dried (MgSO4), and the solvent was evaporated in vacuo. The crude product was distilled over a Vigreux column (0.15 Torr, 91° C.) yielding 85 g (88%) of pure product as colorless oil.
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