Sodium hydride → 7-{(4s)-4-[(1e)-4,4-Difluoro-3-oxo-4-phenylbut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}heptanenitrile

Participants

Reaction Steps

To a solution of alcohol 2-3 (480 mg) in dichloromethane (10 mL) was added Dess-Martin periodanane (1 g) and the mixture was stirred at room temperature for 1 h and concentrated. The residue was co-evaporated with toluene several times, resuspended in ethyl acetate and was allowed to sit at 5° C. overnight. The mixture was filtered and the filtrate was concentrated to give the crude aldehyde 7-[(4S)4-formyl-2-oxo-1,3-oxazolidin-3-yl]heptanenitrile (2-5) which was used directly. To a suspension of NaH (168 mg) in THF was added dimethyl 3,3-difluoro-2-oxo-3-phenylpropylphosphonate (1.1 g) dropwise at 0° C. and the mixture was stirred at the temperature for 30 min. To the mixture was added crude aldehyde 2-5 in THF via a cannula and the mixture was stirred at room temperature for 5 h and quenched with saturated NH4Cl. The mixture was extracted with ethyl acetate and the organic layer was dried and concentrated. The residue was purified by flash chromatography to give the desired product 2-4. 1H NMR (400 MHz, acetone-d6): δ 7.70–7.55 (m, 5H), 7.08 (dd, 1H), 6.95 (d, 1H), 4.70 (m, 1H), 4.52 (t, 1H), 3.30 (m, 1H), 3.00 (m, 1H), 2.48 (t, 2H), 1.70–1.25 (m, 8H).

Provenance & Evidence