Lithium hydroxide, monohydrate → HCID 178524335, compound

HRID 2225199Notes

Reaction equation

HRID 2225199 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-aa4edc4d160a4fe18b2a2b163bf3480a
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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