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

A mixture of 4-(2-pyrimidinyl)-benzaldehyde (1.83 g, 9.94 mmol, prepared as described in WO 9828264), (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 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 mixture was cooled to 0° C., the precipitated solids were removed by filtration, washed with water and air-dried. Recrystallization from 2-propanol provided 1.20 g (57%) of the title compound as a light yellow solid. MS 211 (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 mixture was cooled to 0° C.
10. customthe precipitated solids were removed by filtration
11. washwashed with water
12. customair-dried
13. customRecrystallization from 2-propanol

ORDレコード

ord-4da97e34da684bd08056b982ffd70aea

出典データセット

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06713455B2