Allyl Alcohol → 3-(Quinolin-6-yl)propanal

Temperature

30 °C

Tris(dibenzylideneacetone)dipalladium (480 mg, 0.52 mmol) (Aldrich, Cat. #328774) and tri-tert-butyl-phosphonium tetrafluoroborate (300 mg, 1.0 mmol) in a flask was evacuated and refilled with nitrogen (2 times). 1,4-Dioxane (31 mL) was added followed by consecutive addition of 6-bromoquinoline (7.2 g, 35 mmol) (TCI, Cat. #B2015), 2-propen-1-ol (4.7 mL, 69 mmol) and N-cyclohexyl-N-methyl-cyclohexanamine (8.9 mL, 42 mmol). The reaction vessel was evacuated and refilled with nitrogen (2 times). The reaction mixture was stirred at 30° C. for 24 h. Diethyl ether (30 mL) was added to the reaction mixture and then filtered and washed with diethyl ether. The organic extract was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes (0-50%) to afford the desired product. (˜55%) LCMS (M+H)+: m/z=186.0; (M+H2O+H)+: m/z=204.0.

1. additionrefilled with nitrogen (2 times)
2. customThe reaction vessel was evacuated
3. additionrefilled with nitrogen (2 times)
4. additionDiethyl ether (30 mL) was added to the reaction mixture
5. filtrationfiltered
6. washwashed with diethyl ether
7. extractionThe organic extract
8. concentrationwas concentrated under reduced pressure
9. customThe residue was purified by flash chromatography
10. washeluting with ethyl acetate in hexanes (0-50%)

ORD record

ord-ae16afe4c1404a62a98099c5012112f5

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221824B2