Isopropanol → 1-Quinolin-6-ylcyclopropanecarbaldehyde

Temperature

-2.5 °C

Diisobutylaluminum hydride (1M in THF, 96 mL, 96 mmol) was added to a solution of 1-quinolin-6-ylcyclopropanecarbonitrile (12.4 g, 63.9 mmol) in toluene (120 mL) at −78° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warm to −5 to 0° C., and stirred at that temperature for 3 h. The reaction mixture was cooled to −60° C. Isopropyl alcohol (10 mL) was carefully added dropwise. After stirring for 30 min, the reaction mixture was warmed to −5 to 0° C. The reaction mixture was diluted with ethyl acetate, quenched with water and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over sodium sulfate, filtered through a pad of silica gel eluting with 40% ethyl acetate in hexanes. The filtrate was concentrated to yield the desired product. (12 g, 95.1%).

1. temperatureThe reaction mixture was cooled to −60° C
2. stirringAfter stirring for 30 min
3. temperaturethe reaction mixture was warmed to −5 to 0° C
4. customquenched with water
5. extractionextracted with ethyl acetate
6. washThe combined organic extracts were washed with water, brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered through a pad of silica gel eluting with 40% ethyl acetate in hexanes
9. concentrationThe filtrate was concentrated

ORD record

ord-c00962cf83ca495b81fd172efc6e1077

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767675B2