Sodium Hydroxide → 2-(4-Methoxybenzyl)-2h-tetrazole-5-carboxylic acid

HRID 2384103Notes

Reaction equation

HRID 2384103 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:10]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:9]2[N:8]=[N:7][C:6]([C:4]([OH:5])=[O:3])=[N:10]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13596243ethyl 2-(4-methoxybenzyl)-2H-tetrazole-5-carboxylate

Product 1

HCID 135962442-(4-Methoxybenzyl)-2h-tetrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Next, to a solution of 2-(4-methoxy-benzyl)-2H-tetrazole-5-carboxylic acid ethyl ester (1.5 g, 5.72 mmol) in ethanol (10 mL) is added 1N NaOH (10 mL, 10 mmol) and the mixture is stirred at room temperature for 2 hours. The solvent is removed under reduced pressure and the mixture acidified with 1N HCl. The mixture is extracted with EtOAc and the organic phase is washed with brine and dried over MgSO4. The solvent is removed under reduced pressure to give the title compound; HPLC Retention time 0.73 minutes (condition C): MS 233.2 (M−1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionThe mixture is extracted with EtOAc
  3. washthe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e11a1d8df82e48e69a48863b5d35b036
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

Loading…