Triethylamine → HCID 69728829, Verbindung

Temperatur

0 °C

Triethyl 2-fluoro-2-phosphonoacetate (1.55 mL, 7.64 mmol) was added to a suspension of MgBr2 (1.68 g, 9.12 mmol) in THF (20 mL). The resulting mixture was cooled to 0° C., triethylamine (1.20 mL, 8.61 mmol) was added, and stirring was continued for 1 h at 0° C. A solution of 4-(2-pyrimidinyl)-benzaldehyde (1.00 g, 5.43 mmol, prepared as described in WO 9828264) in THF (10 mL) was aded via cannula and an additional amount of THF (5 mL) was used to rinse the transfer flask and cannula. The resulting mixture was stirred for 3 h at 0° C., quenched with 10% aq. ammonium chloride (5 mL), and concentrated to a small volume. The concentrate was diluted with ethyl acetate (50 mL), washed with 10% aq. ammonium chloride, sat. aq. NaHCO3, and brine (50 mL each), dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 3:1 hexane/ethyl acetate) provided 1.27 g of the title compound as a 3:1 mixture with its E isomer. Recrystallization from 2-propanol provided 0.76 g (51%) of the title compound containing ca. 1% of the E isomer. MS 273 (M+H)+.

1. washto rinse the transfer flask and cannula
2. stirringThe resulting mixture was stirred for 3 h at 0° C.
3. customquenched with 10% aq. ammonium chloride (5 mL)
4. concentrationconcentrated to a small volume
5. additionThe concentrate was diluted with ethyl acetate (50 mL)
6. washwashed with 10% aq. ammonium chloride, sat. aq. NaHCO3, and brine (50 mL each)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customPurification by chromatography (SiO2, 3:1 hexane/ethyl acetate)

ORD-Eintrag

ord-2a3a9c6684774ab4844d241fdb15bf7b

Quelldatensatz

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06825170B2