Triethyl phosphonoacetate → HCID 21666955, Verbindung

Temperatur

0 °C

To a suspension of lithium chloride (0.504 g, 11.9 mmol) in MeCN (20 mL) were added ethyl 2-(diethoxyphosphoryl)acetate (available from Aldrich) (1.91 mL, 9.52 mmol) and DBU (1.42 mL, 9.52 mmol) at room temperature. The mixture was cooled to 0° C., and 4,4,4-trifluorobutanal (available from Matrix Scientific) (1.00 g, 7.93 mmol) was added dropwise. The resulting mixture was warmed to room temperature and stirred overnight. The mixture was partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford (E)-ethyl 6,6,6-trifluorohex-2-enoate 68.B (6:1 E/Z) as a colorless liquid (1.13 g, 73%).

1. temperatureThe resulting mixture was warmed to room temperature
2. customThe mixture was partitioned between water and EtOAc
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with additional EtOAc
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customThe residue was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

ORD-Eintrag

ord-22d2e25626a14b10b50f842b905d91c6

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08030354B2