Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → (E)-3-[4-(2-Pyridinyl)phenyl]-2-propenal

A mixture of 4-(2-pyridinyl)-benzaldehyde (1.76 g, 9.58 mmol), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (6.45 g, 15.02 mmol), and TDA-1 (Tris(3,6-dioxaheptyl)amine, 3.20 mL, 10.00 mmol) in dichloromethane (50 mL) and sat. aq. K2CO3 (50 mL) was heated to reflux for 20 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. Purification by chromatography (SiO2, 3:1 hexane/ethyl acetate) provided 1.69 g (89%) of the title compound as a yellow solid. MS 210 (M+H)+.

1. temperaturewas heated
2. temperatureto reflux for 20 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. customPurification by chromatography (SiO2, 3:1 hexane/ethyl acetate)

ORD record

ord-bad2f943fd7c49719d72604fed49f6af

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06713455B2