Sodium Thiosulfate → HCID 67300896, compound

Participants

Reaction Steps

A suspension of the Dess-Martin periodinane (1.2 equiv, 0.013 mmol, 14 mg) in anhydrous CH2Cl2 (0.5 mL) was treated with a solution of (Z)-1-(1,3,4-thiadiazol-2-yl)-octadec-9-en-1-ol (4 mg, 0.011 mmol) in anhydrous CH2Cl2 (0.5 mL) at room temperature under N2. After 10 h the suspension was diluted with Et2O (10 mL), and poured into a solution of Na2S2O3 (40 mg) in saturated aqueous NaHCO3 (3.4 mL). The mixture was stirred at room temperature for 1 h and the layers were separated. The ethereal layer was washed with saturated aqueous NaHCO3 and H2O, dried over MgSO4, filtered and condensed. Flash chromatography (SiO2, 1.5 cm×15 cm, 2% MeOH—CH2Cl2) afforded the title compound (3 mg, 70% yield) as a dark yellow oil: 1H NMR (CDCl3, 250 MHz) δ 9.29 (s, 1H), 5.41-5.27 (m, 2H), 3.10 (t, 2H, J=7.4 Hz), 2.12-1.88 (m, 4H), 1.84-1.75 (m, 2H), 1.47-1.19 (m, 20H), 0.87 (br t, 3H, J=6.6 Hz); IR (CDCl3) νmax 2936, 2855, 1710, 1610, 1562, 1516, 1426, 1372 cm−1; MALDI-FTMS (DHB) m/z 351.2464 ([M+H]+, C20H34N2OS requires 351.2470).

Provenance & Evidence