Aluminium lithium hydride → 2-(Quinolin-5-yl)propan-1-ol
Reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH3:16])[C:12](OC)=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[N:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH3:16])[CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Methyl 2-(5-quinolyl)propanoate (100 mg, 0.47 mmol) was dissolved in dry THF(10 mL) and cooled to −78° C. on a dry ice/acetone bath. Lithium aluminum hydride (1M in ether, 0.93 mL, 0.93 mmol) was added dropwise. The mixture stirred for 10 minutes while warming to 0° C. The reaction was quenched with KHSO4(1M aq., 1 mL). The mixture was made basic with NaOH(1M aq) and extracted into ethyl acetate. The organics were washed with brine, dried over MgSO4 and then removed under reduced pressure to give 2-(5-quinolyl)-1-propanol (65 mg, 74%). HPLC (10% to 90% acetonitrile in 0.1N aqueous ammonium acetate over 10 min at 2 mL/min using a waters Symmetry C18, 150×4.6 mm column) 2.96 min.