Ethanol → HCID 58335365, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 37h) (46 mg, 0.11 mmol) in dry EtOH (5 mL) under nitrogen was added SnCl2.2H2O (241 mg, 1.07 mmol). The solution was heated to reflux for 4 h. The solution was concentrated in vacuo and the residue was dissolved in EtOAc (5 mL) and treated with sodium potassium tartrate (1M, 5 mL). The mixture was warmed to 50° C. heated at this temperature until the layers visibly separated. The organic layer was separated and the aqueous further extracted with EtOAc (2×5 mL). The organics were pooled, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was taken up in dry DMF (3 mL) and to this solution triethyl orthoacetate (3 mL, excess) was added. The solution was stirred at reflux for 1 h. The solution was concentrated in vacuo and the residue was taken in CH2Cl2 (5 mL) and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, ethyl acetate/petroleum spirit 3:18) to give the title compound (30 mg, 64%). 1H NMR (300 MHz, CDCl3) δ 7.33-7.21 (m, 5H), 4.45-4.40 (t, J=6.6 Hz, 2H), 4.29-4.25 (m, 2H), 3.75-3.72 (t, J=5.7 Hz, 2H), 2.89-2.84 (t, J=7.2 Hz, 2H), 2.65 (s, 3H), 2.59 (s, 3H), 2.19-2.09 (m, 2H), ESIMS m/z [M+H]+ 422.2.

Provenance & Evidence