Sodium Thiosulfate → HCID 68541511, compound

Participants

Reaction Steps

(140) A suspension of the Dess-Martin periodinane (1.2 equiv, 0.025 mmol, 11 mg) in anhydrous CH2Cl2 (0.5 mL) was treated with a solution of 1-([1,3,4]oxadiazol-2-yl)octadec-9-en-1-ol (7 mg, 0.021 mmol) in anhydrous CH2Cl2 (0.5 mL) at rt under N2. After 6 h the suspension was diluted with Et2O (10 mL), and poured into a solution of Na2S2O3 (77 mg) in saturated aqueous NaHCO3 (6.5 mL). The mixture was stirred at rt for 1 h and the layers were separated. The ethereal layer was washed with saturated aqueous NaHCO3 (1×10 mL) and H2O (1×10 mL), dried (MgSO4), filtered and evaporated. Flash chromatography (SiO2, 1.5 cm×15 cm, 2% MeOH—CH2Cl2) afforded 1-([1,3,4]oxadiazol-2-yl)octadec-9-en-1-one (140) (5 mg, 0.016 mmol, 75% yield) as a dark yellow oil: 1H NMR (CDCl3, 250 MHz) d 9.34 (s, 1H), 5.42-5.26 (m, 2H), 3.04 (t, J=7.4 Hz, 2H), 2.12-1.87 (m, 4H), 1.82-1.75 (m, 2H), 1.43-1.19 (m, 20H), 0.88 (br t, J=6.8 Hz, 3H); IR (CDCl3)umax 2940, 2860, 1705, 1612, 1547, 1510, 1423, 1380 cm−1; MALDI-FTMS (DHB) m/z 335.2689 (C20H34N2O2+H+ requires 335.2698).

Provenance & Evidence