Lithium Hydroxide → HCID 57826739, compound

HRID 2392286Notes

Reaction equation

HRID 2392286 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[N:13][CH:12]=1.[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[N:13][CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57826646methyl 5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 57826739HCID 57826739, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylate (400 mg, 1.55 mmol) and 1N LiOH (2.0 ml, 2.0 mmol) in THF (6 ml) was stirred at rt overnight. After removal of THF, the residue was diluted with 10 ml of H2O and washed with DCM (10 ml×2). The aqueous layer was acidified to pH 3 with 1N HCl and then extracted with EtOAc (30 ml×4). The organic layers were combined and concentrated to give 370 mg of the title compound as a white solid. LCMS (ES) m/z 244.0 (M+H)+

Workup

  1. customAfter removal of THF
  2. additionthe residue was diluted with 10 ml of H2O
  3. washwashed with DCM (10 ml×2)
  4. extractionextracted with EtOAc (30 ml×4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dab742cea97048eea48e5e6765c528f5
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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