Allyl bromide → HCID 11109849, compound

Participants

Reaction Steps

To a solution of the compound of step G (1) (208 mg, 756 μmol) in THF (1.5 mL) at −78° C. was added 1 M NaHMDS (832 μL, 832 μmol) dropwise. After 10 minutes, allyl bromide (196 μL, 2.27 mmol) was added in one shot. The reaction was continued at −78° C. until TLC showed complete reaction (˜6 hours). The reaction was quenched with saturated ammonium chloride solution and allowed to come to room temperature. The mixture extracted 3 times with ethyl acetate. The combined organic layers were dried with MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (0% to 10% EtOAc/Hexane gradient) afforded pure product (137 mg, 58%). 1H NMR (500 MHz, CDCl3) δ ppm 0.93-0.81 (m, 6H) 1.35-1.21 (m, 4H) 1.53-1.44 (m, 1H) 1.75-1.66 (m, 1H) 2.34-2.22 (m, 1H) 2.47-2.36 (m, 1H) 3.98-3.86 (m, 1H) 4.82-4.74 (m, 1H) 5.08-4.94 (m, 2H) 5.63 (d, J=7.32 Hz, 1H) 5.87-5.75 (m, 1H) 7.46-7.24 (m, 5H). HPLC retention time: 1.92 min (method A). MS (ESI) (M+H)+ 316.

Provenance & Evidence