Tetrahydrofuran → HCID 69601012, compound

Participants

Reaction Steps

To a solution of 4-2 (0.65 g, 2.7 mmol) in 15 mL CH2Cl2 was added Dess Martin periodinane (1.4 g, 3.2 mmol) portion wise and the resulting solution was stirred for 2 hours. The solution was concentrated in vacuo, to which toluene was added and concentrated thrice to remove acetic acid. The concentrate was then filtered through celite with CH2Cl2 and concentrated in vacuo. The crude product was then diluted in 7 mL of THF and added to a solution of the Wittig reagent dimethyl 2-oxo-3-phenylpropylphosphonate (1.3 g, 5.3 mmol) and 60% sodium hydride (0.2 g, 5.1 mmol) in 7 mL of THF at 0° C. which had been premixed 30 minutes. The reaction mixture was stirred for 15 minutes at the initial temperature and was allowed to warm up to room temperature for 1 hour. The solution was stored at 4° C. overnight, quenched with saturated aqueous ammonium chloride solution and was extracted with ethyl acetate. 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% ethyl acetate/hexanes to yield 350 mg of 4-3 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.37–7.20 (m, 5H), 6.74 (dd, 1H), 6.31 (d, 1H), 4.34 (q, 1H), 3.88 (s, 2H), 3.54–3.44 (m, 2H), 3.01 (dd, 1H), 2.77 (m, 1H), 2.33 (t, 2H), 1.67–1.60 (m, 2H), 1.47–1.30 (m, 4H), 1.28–1.23 (m, 2H); MS (+ESI): m/z 356.9 (M+1)+.

Provenance & Evidence