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

A mixture of 6-quinoxalinecarboxaldehyde (0.62 g, 3.92 mmol, prepared as described in Photochem. Photobiol. 1991, 54, 7), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (2.50 g, 5.82 mmol), and TDA-1 (1.20 mL, 3.75 mmol) in dichloromethane (20 mL) and sat. aq. K2CO3 (20 mL) was heated to reflux for 4 h. The layers were separated and the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2SO4), and concentrated. THF (10 mL) and 10% HCl (10 mL) were added and the mixture was stirred for 1 h at rt. The mixture was cooled to 0° C., the precipitated solids were removed by filtration, washed with water and dried in vacuo to give 0.47 g (65%) of the title compound as a tan solid. MS 185 (M+H)+.

1. temperaturewas heated
2. temperatureto reflux for 4 h
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
5. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. additionTHF (10 mL) and 10% HCl (10 mL) were added
9. temperatureThe mixture was cooled to 0° C.
10. customthe precipitated solids were removed by filtration
11. washwashed with water
12. customdried in vacuo

ORD-Eintrag

ord-d7424d04e2f24310a1dbd88da33e8436

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06713455B2