Reaction #58905

Reaction equation

Diisobutylaluminum hydride

methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate

hydrochloric acid

→

[5-(4-fluorophenyl)-1,2,3-thiadiazol-4-yl]methanol

Yield 76.2%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic layer was washed with saturated brine
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated

Procedure

Diisobutylaluminum hydride (1.5N toluene solution, 10 ml) was added to a solution of methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate (1.19 g) in tetrahydrofuran (30 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was poured into an aqueous dilute hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give [5-(4-fluorophenyl)-1,2,3-thiadiazol-4-yl]methanol (0.80 g, yield 76%) as a yellow oil.

Source