Ethanethiol → HCID 66891866, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of NaH (60% dispersion in mineral oil, 80 mg, 2.0 mmol) in anhyd DMF (0.5 mL) was chilled to 0° C. and charged dropwise with ethanethiol (74 μL, 1.0 mmol). The reaction mixture was removed from the ice-bath and stirred at ambient temperature. After 10 min, additional DMF (0.5 mL) was added to facilitate stirring. To the resulting mixture was added dropwise a solution of 1-{4-[1-ethyl-1-(4-methoxyphenyl)-propyl]-2-methylphenyl}-4,4-dimethylpentan-3-ol (0.10 g, 0.26 mmol) in anhyd DMF (0.7 mL). The reaction mixture was transferred to an oil bath and heated at reflux. After 3 h the mixture was cooled, quenched with satd NH4Cl (50 mL), extracted with Et2O (2×50 mL). The combined extracts were washed with H2O (2×50 mL) and brine, then dried (Na2SO4), concentrated under reduced pressure and chromatographed (silica, EtOAC/Hex, 0:100 to 25:75) to give the title compound (36 mg, 37% non-optimized) as a tacky white solid: 1H-NMR (CD2Cl2) δ 7.00-7.06 (3H, m), 6.90-6.94 (2H, m), 6.71 (2H, d), 4.95 (1H, br s), 3.24 (1H, dd, J=1.8, 10.6), 2.85 (1H, ddd, J=5.1, 10.6, 13.9), 2.54 (1H, ddd, J=6.1, 10.4, 13.9), 2.24 (3H, s), 2.05 (4H, q, J=7.3), 1.72-1.84 (1H, m), 1.42-1.54 (1H, m), 0.88 (9H, s), 0.59 (6H, t, J=7.3).

Provenance & Evidence