Aluminium lithium hydride → 2-(Quinolin-5-yl)propan-1-ol

Temperature

-78 °C

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.

1. temperaturewhile warming to 0° C
2. customThe reaction was quenched with KHSO4(1M aq., 1 mL)
3. extractionextracted into ethyl acetate
4. washThe organics were washed with brine
5. dry with materialdried over MgSO4
6. customremoved under reduced pressure

ORD record

ord-616261477f8e49c4a8a897d8a58bc90f

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06875765B2