Water → 1,2,3-Thiadiazol-4-ylmethanol

HRID 236444

Reaction equation

HRID 236444 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[S:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[N:2]1.[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[N:2]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 254337Ethyl 1,2,3-thiadiazole-4-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 2

HCID 254337Ethyl 1,2,3-thiadiazole-4-carboxylateYield 7%HCID 147274091,2,3-Thiadiazol-4-ylmethanolYield 18%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
23 °C

Procedure

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).

Workup

  1. waitThe stirring was continued for 24 h
  2. stirringAfter stirring for 15 min
  3. customthe ether solution was decanted
  4. extractionthe gum was extracted with ether (5×100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated (5.4 g)
  7. customThe crude material was purified on silica gel column (120 g, 4×16 cm), with ether
  8. washas eluting solvent

Sources & evidence

ORD record
ord-ec5b96bcb93449a993bd202cbbfe9f17
Source dataset
uspto-grants-1987_02
Patent number
US04644061

Linked notes

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