Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → (2E)-3-(6-Quinolinyl)-2-propenal

A mixture of 6-quinolinecarboxaldehyde (1.58 g, 10.05 mmol, prepared as described in U.S. Pat. No. 5,559,256), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (6.45 g, 15.02 mmol), and TDA-1 (3.20 mL, 10.00 mmol) in dichloromethane (50 mL) and sat. aq. K2CO3 (50 mL) was heated to reflux for 5 h. The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. THF (25 mL) and 10% HCl (25 mL) were added and the mixture was stirred for 1 h at rt. The reaction mixture was cooled to 0° C., made basic with 10% NaOH, and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. Chromatography (SiO2, 1:1 hexane/ethyl acetate+0.2% triethylamine) provided a yellow solid that was partitioned between ethyl acetate (20 mL) and 10% HCl (15 mL). The aqueous layer was washed with ethyl acetate (2×20 mL) and then made basic with 10% NaOH. The precipitated solids were collected by filtration, washed with water, and dried in vacuo to give 1.20 g (65%) of the title compound as a light yellow solid. MS 184 (M+H)+.

1. customprepared
2. temperatureto reflux for 5 h
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
5. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. additionTHF (25 mL) and 10% HCl (25 mL) were added
9. temperatureThe reaction mixture was cooled to 0° C.
10. extractionextracted with ethyl acetate (3×25 mL)
11. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
12. dry with materialdried (MgSO4)
13. concentrationconcentrated
14. customChromatography (SiO2, 1:1 hexane/ethyl acetate+0.2% triethylamine) provided a yellow solid
15. customthat was partitioned between ethyl acetate (20 mL) and 10% HCl (15 mL)
16. washThe aqueous layer was washed with ethyl acetate (2×20 mL)
17. filtrationThe precipitated solids were collected by filtration
18. washwashed with water
19. customdried in vacuo

ORD-Eintrag

ord-75163e7710824cac99facc83330079da

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06713455B2