Sodium hexamethyidisilazane → HCID 59517955, compound

Participants

Reaction Steps

To the solution of Ph3PCH3Br (75 mg, 0.21 mmol) in THF (4 mL) was added sodium hexamethyidisilazane (NaHMDS) (1 N, 0.21 mL, 0.21 mmol) at −78° C. After stirring at this temperature for 30 min, Compound 100 (70 mg, 0.21 mmol) was added. The reaction solution was allowed to warm up to room temperature and stirred overnight. The solution was quenched with NH4Cl (20 mL) and extracted with EtOAc (30 mL). The organic portion was collected, dried and concentrated. Column chromatography afforded Compound 101 (42 mg, 60%). 1H NMR (300 MHz, CDCl3) δ 7.63-7.51 (m, 3 H), 7.45-7.38 (m, 1 H), 7.26-7.15 (m, 2 H), 7.04-6.97 (m, 2 H), 6.45 (dd, J=17.4 and 11.1 Hz, 1 H), 5.14 (d, J=17.4 Hz, 1 H), 4.86 (d, J=11.4 Hz, 1 H), 2.37-2.29 (m, 4 H), 1.79-1.72 (m, 4 H); ESMS cacld (C21H19F2NO): 339.1; found: 340.1 (M+H).

Provenance & Evidence