HCID 72472678, compound → HCID 67006420, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-[4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-yl]-propionaldehyde (1.79 g, 4.47 mmol) in THF (45 mL) at −78° C. was treated with allylmagnesium bromide (1 M in Et2O, 5.8 mL, 5.8 mmol) and warmed to 0° C. over 1 h. The reaction mixture was quenched with saturated aqueous NH4Cl, and extracted with EtOAc (2×). The combined organic extracts were washed saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (2→10% EtOAc/CH2Cl2) afforded the title compound (1.3 g, 66%): 1H NMR (CDCl3 400 MHz) δ 7.71 (dd, J=8.1, 1.5 Hz, 2H), 7.53 (dd, J=8.1, 1.5 Hz, 2H), 7.03 (m, 1H), 6.41 (m, 1H), 5.76 (m, 1H), 5.16-5.08 (m, 2H), 4.93 (ddd, J=11.7, 2.9, 2.9 Hz, 1H), 4.32 (dd, J=12.4, 2.2 Hz, 1H), 4.31 (s, 1H), 3.59 (m, 1H), 2.85 (m, 1H), 2.29-2.10 (m, 2H), 1.68-1.43 (m, 4H).

Provenance & Evidence