Sodium Thiosulfate → HCID 67300896, compound

Participants

Reaction Steps

(141) 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 1-([1,3,4]thiadiazol-2-yl)octadec-9-en-1-ol (4 mg, 0.011 mmol) in anhydrous CH2Cl2 (0.5 mL) at rt 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 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]thiadiazol-2-yl)octadec-9-en-1-one (141) (3 mg, 0.008 mmol, 70% yield) as a dark yellow oil: MALDI-FTMS (DHB) m/z 351.2464 (C20H34N2OS+H+ requires 351.2470).

Provenance & Evidence