反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 3-Fluorophenethyl bromide (23, 1.00 g, 12.3 mmol) was diluted in dry DMF (25 mL). Sodium cyanide (1.06 g, 61.6 mmol) was added in one portion, and the mixture was heated to 60° C. under argon for 16 h. The mixture was cooled and concentrated, and the residue was partitioned between EtOAc and H2O (50 mL each). The layers were separated, and the aqueous phase was extracted with EtOAc (2×20 mL). The organic layers were washed with H2O and sat. aq. NaCl (50 mL each), dried over anhydrous sodium sulfate, and concentrated. The resulting oil was purified by flash column chromatography (SiO2), eluting with a gradient of 5% EtOAc in hexanes to 30% EtOAc in hexanes to yield the desired product as a colorless oil (0.638 g, 87%). 1H-NMR (500 MHz; CDCl3): δ 7.31 (td, J=7.9, 6.0 Hz, 1 H), 7.03-6.93 (m, 3 H), 2.96 (t, J=7.4 Hz, 2 H), 2.63 (t, J=7.4 Hz, 2 H).
The mixture was cooled
concentrated
the residue was partitioned between EtOAc and H2O (50 mL each)
The layers were separated
the aqueous phase was extracted with EtOAc (2×20 mL)
The organic layers were washed with H2O and sat. aq. NaCl (50 mL each)
dried over anhydrous sodium sulfate
concentrated
The resulting oil was purified by flash column chromatography (SiO2)
eluting with a gradient of 5% EtOAc in hexanes to 30% EtOAc in hexanes
来源 ID: ord-e888f39008f34601ba259c862562d6eb