Water → 2-(3,5-diethyl-1H-pyrazol-4-yl)-ethanol

HRID 549412Notes

Reaction equation

HRID 549412 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1[C:13]([CH2:19][CH3:20])=[N:14][NH:15][C:16]=1[CH2:17][CH3:18])C.O>O1CCCC1>[CH2:17]([C:16]1[C:12]([CH2:11][CH2:10][OH:9])=[C:13]([CH2:19][CH3:20])[NH:14][N:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 57899303(3,5-diethyl-1H-pyrazol-4-yl)acetic acid ethyl ester

Product 1

HCID 578992212-(3,5-diethyl-1H-pyrazol-4-yl)-ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (190 mg, 4.8 mmol) was added slowly to tetrahydrofuran (10 mL) under 0° C. (3,5-Diethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (1.0 g, 4.8 mol) in tetrahydrofuran (5 mL) was slowly added under nitrogen atmosphere. The reaction was allowed to slowly warm to room temperature and stirred for 16 h. After the reaction was cooled at 0° C., water (0.3 mL) was added slowly and the reaction was stirred for 30 minutes, 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-(3,5-diethyl-1H-pyrazol-4-yl)-ethanol (0.8 g, 100% yield).

Workup

  1. additionwas slowly added under nitrogen atmosphere
  2. temperatureAfter the reaction 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-b621378d3f3c4559a40aceba85c48422
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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