Tetrahydrofuran → HCID 21949529, compound

Participants

Reaction Steps

To a solution of alcohol 1-5 (273 mg) in dichloromethane (5 mL) was added Dess-Martin periodinane (451 mg) and the mixture was stirred at room temperature for 1 h and concentrated. The mixture was resuspended in ether, filtered and the filtrate was washed with saturated NaHCO3 and dried over Na2SO4. Filtration and concentration in vacuo afforded the crude aldehyde Ethyl 7-(4-formyl-2-oxo-1,3-oxazolidin-3-yl)heptanoate (1-7) which was used directly without further purification. To a suspension of NaH (47 mg) in THF (6 mL) was added dimethyl 2-oxo-3-phenylpropylphosphonate (282 mg) at 0° C. (formed a white slurry) and the mixture was stirred for an additional 1 h. To the mixture was then added aldehyde 1-7 (145 mg) in THF (4 mL) via cannula and the resultant mixture stirred at room temperature for 2 h and quenched with saturated NH4Cl. The mixture was then extracted with ethyl acetate (3×) and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography using ethyl acetate/hexanes (1:1) as the eluent to give the desired product 1-6. 1H NMR (400 mg, acetone-d6): δ 7.36–7.26 (m, 5H), 6.86 (dd, 1H), 6.43 (d, 1H), 4.57 (m, 1H), 4.50 (t, 1H), 4.12–3.96 (m, 5H), 3.28 (m, 1H), 2.96 (m, 1H), 2.28 (t, 2H), 1.65–1.45 (m, 4H), 1.35–1.25, m, 4H), 1.22 (t, 3H).

Provenance & Evidence