Triethylamine → HCID 69728829, compound

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence