Butanethiol → Dibutyl sulfide

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).

1. customThe reaction mixture was quenched with saturated NH4Cl
2. extractionextracted with ether
3. washThe combined organic phase was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe crude residue was purified by flash chromatography
7. washeluting with 1% AcOEt-Hexanes

ORD record

ord-2fdfd398bb88420caf1812a8e17173fb

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090651B2