Sodium hydride → HCID 69601148, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-4 (0.73 g, 3.4 mmol) in 10 mL DMF was added 60% sodium hydride (140 mg, 3.5 mmol) and the resulting solution was stirred for 1 hour at 50° C. whereupon 7-bromoheptanonitrile (1.1 mL, 6.8 mmol) and tetrabutylammonium iodide (50 mg) were added. The solution was stirred at 50° C. overnight afterwhich it was cooled to room temperature, slowly poured into saturated aqueous ammonium chloride solution and was extracted with ether. The organic phases were then combined and sequentially washed with H2O, brine and dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 40–50% ethyl acetate/hexanes to yield 970 mg of 4-1 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 4.63 (m, 1H), 4.04–3.68 (m, 3H), 3.68–3.58 (m, 1H), 3.55 (m, 2H), 3.42 (dd, 1H), 3.22–3.04 (m, 2H), 2.36 (t, 2H), 1.86–1.44 (m, 12H), 1.38–1.30(m, 2H); MS (+ESI): m/z 327.2 (M+1)+.

Provenance & Evidence