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

HRID 1802785Notes

Reaction equation

HRID 1802785 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 mmol) 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-b242c83c868c4d498065b46da27910d8
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

Loading…