Sodium bis(trimethylsilyl)amide → HCID 66577527, compound

Participants

Reaction Steps

NaHMDS (5.35 ml, 10.70 mmol) was added to methyltriphenylphosphonium bromide (3822 mg, 10.70 mmol) in THF (53.500 ml) at RT. The reaction was stirred at RT for 1 hr before 4-(pent-4-en-1-yl)dihydro-2H-pyran-3(4H)-one (900 mg, 5.35 mmol) in THF (2 mL) was added at 0° C. The reaction mixture was stirred at room temperature for 2 hr. The mixture was cooled and quenched with aqueous NH4Cl. The reaction mixture was extracted with diethyl ether (3×20 mL). The combined organic fractions were washed with water and brine (saturated, 100 mL), dried, filtered and the solvent was evaporated under reduced pressure (400 mmhg). The residue was purified by column chromatography on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.75-5.89 (m, 1H), 4.92-5.06 (m, 2H), 4.86 (s, 1H), 4.77 (t, 1H, J=1.5 Hz), 4.12 (d, 1H, J=12.1 Hz), 3.86-3.96 (m, 2H), 3.57-3.65 (m, 1H), 2.15-2.24 (m, 1H), 2.00-2.12 (m, 2H), 1.81-1.91 (m, 1H), 1.64-1.76 (m, 1H), 1.21-1.52 (m, 4H).

Provenance & Evidence