Diethyl Ether → HCID 88289706, compound

Participants

Reaction Steps

To a 4-neck 500 ml flask, equipped with a condenser, mechanical stirrer, thermometer, and nitrogen inlet, was added sodium hydride (3.9 g, 153 mmol) and THF (250 ml) under nitrogen. 2-octyl-2-cyanopropionate (20 g, 115 mmol) was added over 10 min. and the reaction mixture was stirred for 1 hour at room temperature. A solution of phenylselenium bromide, prepared by the above method, was added by syringe. The reaction mixture was stirred for 1 hour and added to 250 ml each of ether and sat. aq. NaHCO3. The organic layer was washed twice with 250 ml of H2O and once with 250 ml sat. aq. NaCl. The organic layer was separated, dried (MgSO4) and filtered. Solvent was removed under reduced pressure. Yield=43.2 g (quant.); NMR δ (CDCl3) 7.75 (d, 2H), 7.40 (m, 3H), 4.85 (m, 2H), 1.80 (s, 3H), 0.8-1.70 (m, 16H); IR (neat) 2333, 1734, 1251 cm-1.

Provenance & Evidence