4-Chlorobutyrophenone → 7-Chloro-2-methyl-4-phenylhept-1-en-4-ol
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH3:13][C:14](=[CH2:18])[CH2:15][Mg]Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([OH:6])[CH2:15][C:14]([CH3:18])=[CH2:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound 4-chloro-1-phenylbutan-1-one (3.64 g, 0.02 mol) in THF (60 mL) was added (2-methylallyl)magnesium chloride (60 mL, 1 mol/L) at −78° C. The mixture was stirred at room temperature for 1 h. TLC showed the disappearance of the starting material. The mixture was quenched with satd aq NH4Cl and extracted with EtOAc. The combined organic phase was dried over Na2SO4 and concentrated to give the crude final product, which was purified by chromatography to afford the compound 7-chloro-2-methyl-4-phenylhept-1-en-4-ol (4.2 g, 90%).