Sodium Azide → 1,1,1-Trifluoro-2-(2H-tetrazol-5-yl)butan-2-ol

HRID 922761Notes

Reaction equation

HRID 922761 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3](=[O:6])[CH2:4][CH3:5].C[Si]([C:13]#[N:14])(C)C.[N-:15]=[N+:16]=[N-:17].[Na+]>[Cl-].[Zn+2].[Cl-].O>[F:1][C:2]([F:8])([F:7])[C:3]([C:13]1[N:14]=[N:15][NH:16][N:17]=1)([OH:6])[CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 82115Trimethylsilyl cyanideHCID 2382881,1,1-Trifluorobutan-2-one

Product 1

HCID 895452101,1,1-Trifluoro-2-(2H-tetrazol-5-yl)butan-2-ol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

To 1,1,1-trifluorobutan-2-one (5.0 g, 39.7 mmol, 1.0 equiv) was slowly added trimethylsilylcyanide (4.7 g, 47.6 mmol, 1.2 equiv) and the resulting mixture stirred overnight at ambient temperature. To the resulting mixture was added water (80 mL) followed by zinc chloride (5.4 g, 39.7 mmol, 1.0 equiv) and sodium azide (3.1 g, 47.1 mmol, 1.2 equiv) and the mixture was heated at 80° C. for three hours. The mixture was cooled to room temperature and the precipitate was filtered and dried in vacuo to afford 1,1,1-trifluoro-2-(2H-tetrazol-5-yl)butan-2-ol (3-3) as a white solid. LRMS m/z (M+H)+ 197.0 found, 197.1 required.

Workup

  1. temperaturethe mixture was heated at 80° C. for three hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3c6218f2443643909ecb6600d1b7f375
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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