Water → 1,2,3-Thiadiazol-4-ylmethanol

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyl 1,2,3-thiadiazol-4-ylcarboxylate (18.35 g, 0.116 mol) in ether (400 mL) was added portionwise lithium aluminum hydride (2.47 g, 0.065 mol) over 1 h period. The reaction mixture was stirred at 23° C. for 7 h and treated with lithium aluminum hydride (2.47 g, 0.065 mL). The stirring was continued for 24 h before adding successively water (7 mL), 15% sodium hydroxide solution (7 mL) and water (21 mL). After stirring for 15 min, the ether solution was decanted and the gum was extracted with ether (5×100 mL). The ether extracts were combined, dried (MgSO4) and concentrated (5.4 g). The crude material was purified on silica gel column (120 g, 4×16 cm), with ether as eluting solvent to give 1.3 g (7%) of ethyl 1,2,3-thiadiazol-4-ylcarboxylate and 2.45 g (18%) of 1,2,3-thiadiazol-4-ylmethanol; ir (film)νmax : 3380 (OH) cm-1 ; 1Hmr (CDCl3)δ: 2.31 (1H, s, OH), 5.22 (2H, s, CH2O), 8.50 (1H, s, H of thiadiazole).

Provenance & Evidence