Tetrahydrofuran → HCID 178520018, compound

Participants

Reaction Steps

To a solution of cyclopropylmagnesiumbromide (37 ml, 0.5 M/THF, 18.4 mmol at 0° C. was slowly added a THF solution of ethyl 5-mercapto-1,3,4-thiadiazole-2-carboxylate (1 g, 5.3 mmol). When half the solution was added, the cooling bath was removed and the rest of the solution was added. The mixture was stirred at room temperature for 4 hours then partitioned between aqueous NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted with Et2O. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue chromatographed on silica gel (hexanes:acetone, 95:5) to give the title compound. 1H NMR (400 MHz, acetone-d6): 4.75 (s, 1H), 1.39-1.26 (m, 2H), 0.67-0.38 (m, 8H).

Provenance & Evidence