Synthesis of Bis(4-Methoxybenzyl)Diselane Derivative

(The reaction
was
carried out under a nitrogen atmosphere.) Sodium borohydride
(0.4 g, 10.6 mmol) was added portionwise to a solution of 1,2-bis(4-methoxybenzyl)diselane
(1.0 g, 2.5 mmol) in EtOH/DMF (30 mL, 1:1, v/v), and the reaction
mixture was stirred for 2 h at room temperature. 2-Bromoethylamine
hydrobromide (1.3 g, 6.3 mmol) was then dissolved in EtOH (5 mL) and
added dropwise at 0 °C. The solution was warmed to room temperature
and stirred overnight. The solvent was removed to dryness under a
stream of nitrogen. The obtained product was dissolved in a saturated
aqueous solution of NaHCO₃, and the aqueous layer was extracted
with ethyl acetate (3×). The organic layer was washed with brine
and dried over anhydrous MgSO₄. The solvent was removed
on a rotary evaporator to give a white solid product. Yield 0.55 g
(90%). ¹H NMR (500 MHz, MeOD): δ = 7.24–7.22
(m, 2H), 6.85–6.83 (m, 2H), 3.78 (s, 2H), 3.77 (s, 3H), 2.80
(t, J = 6.9 Hz, 2H), 2.60 (t, J =
6.9 Hz, 2H); ¹³C{¹H} NMR (126 MHz, MeOD): δ
= 158.7, 131.3, 129.6, 113.5, 54.3, 40.6, 25.5, 25.0; ⁷⁷Se NMR (114 MHz, MeOD): δ = 217.8; calculated m/z [M + H]⁺: 246.0392; found m/z [M + H]⁺: 246.0344 for C₁₀H₁₅NOSe.