Lithium diisopropylamide → HCID 118098707, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 10B (345 mg, 0.893 mmol) in THF (5 mL) at −78° C., was added LDA (2 M, heptane, THF and ethylbenzene) (0.536 mL, 1.071 mmol). The red/black mixture was stirred at −78° C. for 20 min, then a solution of 2,2-difluoroethyl trifluoromethanesulfonate (210 mg, 0.982 mmol) in THF (0.5 mL) was added dropwise. The reaction was removed from the cooling bath and was stirred at rt for 4 h. The reaction mixture was quenched with sat. NH4Cl, diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (loaded in chloroform onto a 12 g column and eluted with a gradient from 0 to 50% ethyl acetate/hexanes) to give 10C (70 mg, 0.155 mmol, 17.41% yield) pale yellow oil. MS (ESI) m/z: 450.9 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 8.15 (d, J=7.91 Hz, 1H) 7.97-8.11 (m, 1H) 7.50 (d, J=7.47 Hz, 1H) 7.24-7.43 (m, 5H) 5.10-5.29 (m, 2H) 4.57-4.87 (m, 2H) 4.00-4.39 (m, 3H) 2.91 (br. s., 3H) 2.57-2.87 (m, 1H) 2.19 (s, 1H) 1.05-1.33 (m, 3H).

Provenance & Evidence