Dichloromethane → Methyl 11-thioacetylundecanoate

Participants

Reaction Steps

Compound 103 (17.8 g, 64 mmol), thioacetic acid (9.7 g, 9.0 ml, 128 mmol), methyltrioctylammonium chloride (0.5 g), cesium carbonate (25 g, 77 mmol), dichloromethane (95 ml) and water (95 ml) were stirred at room temperature for 15 h. The reaction was monitored by TLC (SiO2, ethyl acetate:isooctane, 1:5). The mixture was extracted with dichloromethane and the combined extracts were dried (Na2SO4) and concentrated. Distillation gave pure 104 (15.6 g, 89%) with b.p. 137°-139° (0.1 torr) and m.p. <25° (from isooctane). 1H-NMR (CDCl3, Me4Si) δ 3.67 (s, 3H, MeO), 2.86 (t, 2H, J=7.1 Hz, S--CH2), 2.32 (s, 3H, MeCO), 2.30 (t, 2H, J=7.7 Hz, CH2CO). 13C-NMR (CDCl3, Me4Si) δ 195.9, 174.1 (CO), 51.3, 34.0, 30.5, 29.4, 29.3, 29.2, 29.1, 29.0, 28.9, 28.7, 24.8.

Provenance & Evidence