[CH3:1][CH2:2][CH2:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7].[CH2:9]([Mg]Br)[CH:10]=[CH2:11].C(Br)C=C.[NH4+].[Cl-].Cl>C(OCC)C>[OH:8][C:4]([CH2:9][CH2:10][CH3:11])([CH2:5][CH2:6][CH3:7])[CH2:3][CH:2]=[CH2:1]
113 g of 4-heptanone in 1000 ml of dry diethyl ether was slowly added to a solution of allylmagnesium bromide, prepared from 36.5 g of Mg and 178 g of allyl bromide in 500 ml dry diethyl ether. After the addition the mixture was refluxed for 10 hrs. The reaction mixture was poured on a mixture of 150 g ice, 450 ml of 20% NH4Cl and 350 ml of 5M HCl. The ether phase was separated and the water phase extracted with diethyl ether (3×100 ml). The combined organic phases were then washed with a Na2CO3 -solution and water, dried with Na2SO4 and evaporated. The residue was distilled. Yield: 142 g (b.p. 38°-40° C./0.1 torr)
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