Acetic Acid → 1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanol

HRID 2422728Notes

Reaction equation

HRID 2422728 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([C:13](=[O:15])[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].C(O)(=O)C>CO>[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([OH:15])[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 252640991-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanone

Product 1

HCID 248533921-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanolYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl}ethanone (96.89 g, 479 mmol) in methanol (1000 mL) was cooled in an ice/water bath. Sodium borohydride (29 g, 767 mmol) was added over 1 hour 30 minutes. After stirring for 40 minutes aq. acetic acid (70%, 20 mL) was added and the mixture was concentrated. Dichloromethane (400 mL) was added to the residue and was extracted with saturated aqueous sodium hydrogen carbonate (500 mL). The aqueous layer was extracted with dichloromethane (170 mL), and the combined organic layer was washed with aqueous hydrochloric acid (0.5 M, 250 mL), followed by aqueous hydrogen carbonate (280 mL), then washed with brine (500 mL), dried over sodium sulfate, filtered and concentrated to give the title product (95 g, 97%).

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated
  3. additionDichloromethane (400 mL) was added to the residue
  4. extractionwas extracted with saturated aqueous sodium hydrogen carbonate (500 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (170 mL)
  6. washthe combined organic layer was washed with aqueous hydrochloric acid (0.5 M, 250 mL)
  7. washwashed with brine (500 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-34a82a5d8cc34dda9498dced8f918706
Source dataset
uspto-grants-2011_06
Patent number
US07960422B2

Reaction notes

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