Methyl 4-pyridin-3-ylbenzoate → [4-(Pyridin-3-yl)phenyl]methanol
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=2)[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-pyridin-3-yl-benzoic acid methyl ester (124 mg in 5.0 mL dry methylene chloride) at -78° C. was added 1.46 mL of a 1M solution of diisobutylaluminum hydride in methylene chloride and the mixture stirred at low temperature. After 2 hours, the reaction was quenched by the addition of acetone, warmed to room temperature and stirred for 20 minutes with 1.5 mL of a 1M solution of tartaric acid. At this time the mixture was extracted with methylene chloride and the combined organics dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then methylene chloride:methanol, 95:5) gave the title compound (104 mg).