Water → HCID 86689986, compound

Participants

Reaction Steps

To 2-hydroxy-4-(methylthio)butanoic acid (Alimet 88%) (10.1 g, 59.2 mmol) was added 1-tetradecanol (7.57 g, 35.3 mmol), p-toluenesulfonic acid (0.55 g, 2.9 mmol) in toluene (50 mL) in a round bottom flask that was fitted with a Dean Stark trap and reflux condenser. The resulting mixture was heated to reflux with removal of water overnight. The reaction was cooled to room temperature and then diluted with ethyl acetate (65 mL) and washed with sat. NaHCO3 (3×30 mL), water (1×30 mL), dried over magnesium sulfate, filtered and evaporated to give a dark oil. The oil was purified by silica gel chromatography with 0-30% ethyl acetate/heptane to give a light yellow oil (3.34 g, 24%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.11-1.38 (m, 22 H) 1.56 (t, J=6.20 Hz, 2 H) 1.76-1.99 (m, 2 H) 1.99-2.10 (m, 8 H) 2.51-2.64 (m, 4 H) 3.99-4.15 (m, 2 H) 4.16-4.32 (m, 1 H) 5.00-5.16 (m, 1 H) 5.51-5.69 (m, 1 H).

Provenance & Evidence