Butanethiol → Dibutyl sulfide

Participants

Reaction Steps

n-Butanethiol (0.69 mL, 6.4 mmol) was added dropwise to a cold suspension of NaH (60% oil dispersion, 307 mg, 7.7 mmol) in DMF (10 mL). After 30 min, the resulting solution was treated with 3-methoxymethoxybenzyl chloride (40) (595 mg, 3.2 mmol) and stirred for an additional hour at room temperature. The reaction mixture was quenched with saturated NH4Cl and extracted with ether. The combined organic phase was washed with brine, dried over Na2SO4, and concentrated. The crude residue was purified by flash chromatography eluting with 1% AcOEt-Hexanes to yield n-butylsulfide 42 (248 mg, 32%). 1H NMR (400 MHz, CDCl3) δ: 0.90 (t, J=7.3 Hz, 3H, —CH3), 1.40 (m, 2H, —CH2—CH2), 1.56 (m, 2H, —CH2—CH2), 2.44 (t, J=7.5 Hz, 2H, —CH2—S), 3.50 (s, 3H, OMe) 3.69 (s, 2H, —CH2—S), 5.20 (s, 2H, —CH2—O), 6.96 (d, J=7.2 Hz, 1H, Ar), 6.98 (d, J=7.3 Hz, 1H, Ar), 7.01 (s, 1H, Ar), 7.24 (t, J=7.8 Hz, 1H, Ar).

Provenance & Evidence