[4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol → (+/-)-4-(5-(4-(2-Methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)-1-(1-hydroxyethyl)benzene
Reaction equation
[CH3:1][CH:2]([CH3:23])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1.[CH3:24][Mg]I>C1COCC1>[CH3:1][CH:2]([CH3:23])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH:21]([OH:22])[CH3:24])=[CH:19][CH:20]=3)[N:11]=2)=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 0.5 g (1.63 mmol) of Aldehyde 1 in 10 mL of THF was treated with 1.1 mL (3.3 mmol) of methylmagnesium iodide (3.0 M in diethyl ether) at −78° C. and was allowed to warm to rt over 30 min. The resulting mixture was quenched with 5 mL of 1 N HCl and was extracted with 30 mL of ethyl acetate. The extract was washed, dried and concentrated to afford the title compound: ESI-MS 323 (M+H); LC-1: 4.2 min.