Lithium hydroxide, monohydrate → HCID 178524335, compound

HRID 1374270Notes

Reaction equation

HRID 1374270 reaction equation
C(CC[N:5]1[C:9]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15]C)=[O:14])=[N:8][N:7]=[N:6]1)#N.O.[OH-].[Li+]>C1COCC1.O.Cl>[NH:8]1[C:9]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[N:5][N:6]=[N:7]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21075151methyl 3-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)benzoate

Product 1

HCID 178524335HCID 178524335, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation H7, Step 3: To a solution of methyl 3-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)benzoate (180 mg, 0.7 mmol) in 20 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (50 mg, 2.1 mmol) in 5.0 mL of water. The reaction mixture was stirred at RT for 16 h. THF was removed under reduced pressure to give a yellow oil which was diluted with 10 mL of 1 N HCl. The aqueous phase was extracted with EtOAc (2×25 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford 100 mg (58% yield) of 3-(1H-tetrazol-5-yl)benzoic acid. MS found: (M+H)+=191.

Workup

  1. customPreparation H7, Step 3
  2. customTHF was removed under reduced pressure
  3. customto give a yellow oil which
  4. extractionThe aqueous phase was extracted with EtOAc (2×25 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e987234b93643aabc3f6e28b78bf8f1
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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