Water → 2-(1-isopropyl-1H-tetrazol-5-yl)-ethanol

HRID 549415Notes

Reaction equation

HRID 549415 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1[N:13]=[N:14][N:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)C.C([O:23][C:24](=O)[CH2:25][C:26]1[N:30]([CH:31]([CH3:33])[CH3:32])[N:29]=[N:28][N:27]=1)C.O>O1CCCC1>[CH:17]([N:15]1[N:14]=[N:13][C:12]([CH2:11][CH2:10][OH:9])=[N:16]1)([CH3:19])[CH3:18].[CH:31]([N:30]1[C:26]([CH2:25][CH2:24][OH:23])=[N:27][N:28]=[N:29]1)([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 57899268(2-isopropyl-2H-tetrazol-5-yl)-acetic acid ethyl esterHCID 57899300(1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl ester

Product 2

HCID 578992162-(2-isopropyl-2H-tetrazol-5-yl)-ethanolHCID 578992222-(1-isopropyl-1H-tetrazol-5-yl)-ethanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (2.1 g, 10 mmol) was added slowly to tetrahydrofuran (30 mL) at 0° C. and a mixture of (2-isopropyl-2H-tetrazol-5-yl)-acetic acid ethyl ester and (1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (2 g, 10 mmol) in tetrahydrofuran (20 mL) was added under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 16 h. After the resulting mixture was cooled at 0° C., water (0.3 mL) was added slowly, and the reaction was stirred for 30 minutes and filtered through a short silica gel column, which was rinsed with ethyl acetate followed by 20% methanol/methylene chloride. The solution was concentrated in vacuo to provide 2-(2-isopropyl-2H-tetrazol-5-yl)-ethanol and 2-(1-isopropyl-1H-tetrazol-5-yl)-ethanol (1.5 g, 95% yield).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. temperatureAfter the resulting mixture was cooled at 0° C.
  3. stirringthe reaction was stirred for 30 minutes
  4. filtrationfiltered through a short silica gel column, which
  5. washwas rinsed with ethyl acetate
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-44273069fccb4041a5949b41acee5d13
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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