Sodium bis(trimethylsilyl)amide → HCID 66579389, compound

Participants

Reaction Steps

To a mixture of methyltriphenylphosphonium bromide (0.920 g, 2.58 mmol) in TI IF (10 mL) under N2 at it was added NaHMDS (2M in THF, 1.30 mL, 2.58 mmol). The mixture was stirred at rt for 1 hr. 4-(1,4,8-trioxaspiro[4.5]dec-6-yl)butanal (0.276 g, 1.29 mmol) was then added and the reaction was stirred at it for 1 hr. It was quenched with sat'd. aq. NH4Cl and extracted 3× with Et2O. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.75-5.86 (m, 1H), 4.91-5.03 (m, 2H), 3.91-4.05 (m, 4H), 3.78-3.90 (m, 2H), 3.62-3.71 (m, 1H), 3.43 (dd, 1H, J=9.0 Hz, 11.2 Hz), 1.98-2.12 (m, 2H), 1.11-1.81 (m, 7H).

Provenance & Evidence