Hydrochloric Acid → HCID 178443124, compound

Participants

Reaction Steps

Thioacetic acid (35 mg, 0.38 mmol) in methanol (20 ml) was treated successively with sodium methoxide (50 mg, 0.9144 mmol) and bromide 8 (105 mg, 0.381 mmol) and stirred at r.t. for 2 d. The reaction mixture was diluted in water and acidified with cold conc. aq. HCl. The aqueous layer was extracted with hexanes, dried (MgSO4) and concentrated invacuo to afford a crude residue was purified by flash column chromatography (eluent gradient elution 65-75% EtOAc in Hexanes) to afford the pure 4 as a viscous oil (105 mg, 0.367 mmol, 96%); δH(270 MHz, CDCl3); 0.86 (3H, t, J 6.8), 1.35 (14H, m), 1.60 (2H, m), 2.00 (4H, m), 2.65 (21, t, J 7.4), 3.24 (2H, s), 5.34 (2H, m) and 10.0 (1H, br s); δC(67.5 MHz, CDCl3) 14.20, 22.76, 27.09, 27.31, 28.45, 28.89, 29.32, 29.35, 29.35, 29.83, 31.95, 32.82, 33.54, 129.44, 130.36 and 176.77; MS (CI) 304 (M+NH4)+; HRMS: Found [M+NH4]+ 304.230876. Calc. for C16H34NO2S: [M+NH4]+0304.231026.

Provenance & Evidence