Water → HCID 17962027, compound

HRID 349521Notes

Reaction equation

HRID 349521 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:12]([NH:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11](/[CH:33]=[CH:34]/[C:35](OCC)=[O:36])[CH:10]=[N:9]1.[F-].[K+].O>O1CCCC1>[CH3:7][N:8]1[C:12]([NH:13][C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:11]([CH2:33][CH2:34][CH2:35][OH:36])[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 21226445Aluminium lithium hydrideHCID 69819494HCID 69819494, compound

Product 1

HCID 17962027HCID 17962027, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (5.7 g, 150 mmol) in tetrahydrofuran (200 ml) was added ethyl (E)-3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)acrylate (21.9 g, 50 mmol) at room temperature. The mixture was stirred at room temperature for 1 hour. After cooling on an ice bath, potassium fluoride (34 g) and water (10 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo, and the residue was dissolved in chloroform. The solution was washed with 10% aqueous citric acid solution. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The oily residue was purified by column chromatography on silica gel eluting with chloroform to give 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propanol (14.8 g) as a solid.

Workup

  1. temperatureAfter cooling on an ice bath
  2. customThe insoluble materials were removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed with 10% aqueous citric acid solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was purified by column chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-b8cc17f5a39d404480a8162125197fab
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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