4-(Cyclopropylmethyl)benzaldehyde → HCID 19010837, compound
Reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH:6]1([CH2:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH2:8][CH2:7]1>C(OCC)C>[CH:6]1([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:14]([OH:15])[CH2:3][CH:2]=[CH2:1])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of allylmagnesium bromide (1.0M in diethyl ether, 3 ml) in diethyl ether (5 ml) was added dropwise 4-(cyclopropylmethyl)benzaldehyde (240 mg) in diethyl ether (2 ml) at 0° C. After 15 minutes, the reaction mixture was quenched by aqueous ammonium chloride and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (85:15) to give 1-[4-(cyclopropylmethyl)phenyl]-3-buten-1-ol (229 mg) as an oil.