Sodium Hydroxide → [3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]-ethyl]phenoxy]acetic acid

HRID 1031945Notes

Reaction equation

HRID 1031945 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]2[N:9]=[N:10][N:11]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=3)[O:18][CH2:19][C:20]([O:22]C)=[O:21])[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:27]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[N:9]=[N:10][N:11]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=3)[O:18][CH2:19][C:20]([OH:22])=[O:21])[N:12]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10071242methyl [3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]ethyl]phenoxy]acetate

Product 1

HCID 10319609[3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]-ethyl]phenoxy]acetic acidYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]ethyl]phenoxy]acetate (0.84 g, 2 mmol), 3N, NaOH solution (2.00 mL, 6 mmol) and methanol (35 mL) was heated for 10 minutes on a steam bath. The methanol was evaporated, the residue diluted with water and acidified to pH=1 with 1N HCl solution. The mixture was extracted three times with CH2Cl2, the combined extracts washed with saturated sodium chloride solution and dried over sodium sulfate. Evaporation of the solvent left an oil which was chromatographed on a column of silica gel using a mixture of chloroform and methanol (93:7) as eluent to give [3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]-ethyl]phenoxy]acetic acid (0.50 g, 61%) as a colorless oil.

Workup

  1. temperaturewas heated for 10 minutes on a steam bath
  2. customThe methanol was evaporated
  3. additionthe residue diluted with water
  4. extractionThe mixture was extracted three times with CH2Cl2
  5. washthe combined extracts washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent
  8. waitleft an oil which
  9. customwas chromatographed on a column of silica gel using
  10. additiona mixture of chloroform and methanol (93:7) as eluent

Sources & evidence

ORD record
ord-86d906d9dbfb4e1dae6d77cb636ff8b3
Source dataset
uspto-grants-1990_09
Patent number
US04956376

Reaction notes

Loading…