Diisobutylaluminum hydride → 4-(Oxazol-2-yl)-benzyl alcohol
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[O:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl-4-(oxazol-2-yl)-benzoate (0.203 g, 1 mmol) in CH2Cl2 (10 mL) 0° C. was added DIBAL-H (4 mL of a 1.0M solution in dichloromethane, 4 mmol) over 10 minutes. The resultant solution was stirred at 0° C. for 2 hours then quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL) and the biphasic mixture stirred rapidly for 60 minutes. The phases were separated and the aqueous layer extracted with CH2Cl2 (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered, concentrated and purified by chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title alcohol (0.156 g, 89%). 1H NMR (CDCl3) δ 3.42 (t, 1H, J=6.0 Hz (OH)), 4.77 (s, 2H, J=6.0 Hz), 7.24 (s, 1H), 7.47 (d, 2H, J=7.8 Hz), 7.71 (s, 1H), 8.05 (d, 2H, J=7.8 Hz).