Water → (1-Trityl-1H-pyrazol-4-yl)methanol

HRID 1458580Notes

Reaction equation

HRID 1458580 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:14]2[CH:18]=[C:17]([C:19](OCC)=[O:20])[CH:16]=[N:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>O1CCCC1>[OH:20][CH2:19][C:17]1[CH:16]=[N:15][N:14]([C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10523968Ethyl 1-tritylpyrazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10688521(1-Trityl-1H-pyrazol-4-yl)methanolYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1M solution in tetrahydrofuran, 4.45 ml, 4.45 mmol) was added dropwise to a stirred solution of ethyl 1-(triphenylmethyl)-pyrazole-4-carboxylate (2.27 g, 5.93 mmol) in anhydrous tetrahydrofuran (300 ml) under nitrogen at 0° C. After 1 h, the mixture was treated sequentially with water (3 ml), 15% aqueous sodium hydroxide (3 ml) and water (6 ml). The mixture was filtered through Arbocel filter aid, the filtrate was dried (MgSO4) and concentrated under reduced pressure, to give 4-hydroxymethyl-1-(triphenylmethyl) pyrazole (1.746g, 86%), as a white solid.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. dry with materialthe filtrate was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c55e703548c34ca4a24485a3765009a8
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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