Hydrochloric Acid → [5-(4-Fluorophenyl)-1,2,3-thiadiazol-4-yl]methanol

HRID 30627Notes

Reaction equation

HRID 30627 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22][N:21]=[N:20][C:19]=2[C:23](OC)=[O:24])=[CH:14][CH:13]=1.Cl>O1CCCC1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[S:22][N:21]=[N:20][C:19]=2[CH2:23][OH:24])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 69207857Methyl 5-(4-fluorophenyl)-1,2,3-thiadiazole-4-carboxylate

Product 1

HCID 69206022[5-(4-Fluorophenyl)-1,2,3-thiadiazol-4-yl]methanolYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2b1b18a4158432dbb85475ba25d74f1
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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