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Trityl chloride → HCID 15475336, compound

HRID 566238
Notes
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Reaction equation

HRID 566238 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][OH:8])=[N:2]1.[NH:9]1[CH:13]=[C:12]([CH2:14][CH2:15][OH:16])[CH:11]=[N:10]1.C(N(CC)CC)C.[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.O>[C:25]1([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:1]2[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][OH:8])=[N:2]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1.[C:25]1([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:9]2[CH:13]=[C:12]([CH2:14][CH2:15][OH:16])[CH:11]=[N:10]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 42936042-(1H-Pyrazol-4-yl)ethanolHCID 178520322HCID 178520322, compound

Product 2

HCID 15475336HCID 15475336, compoundHCID 154753372-[1-(Triphenylmethyl)-1H-pyrazol-4-yl]ethan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-pyrazolyl)ethanol and 2-(4-pyrazolyl)ethanol (2.4:1) (2.50 g) was dissolved in DMF (30 ml). To the solution were added, while stirring, triethylamine (2.26 g) and trityl chloride (6.22 g). The mixture was stirred at 25° C. for one hour, then at 40° C. for one hour. The reaction mixture was diluted with water, which was subjected to extraction with ethyl acetate. The organic layer was washed with an aqueous saline solution, which was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was purified by means of a column chromatography (carrier: silica gel, 300 g, developing solvent: ethyl acetate-hexane, 1:1) to afford 2-(1-triphenylmethyl-3-pyrazolyl)ethanol (3.75 g) and 2-(1-triphenylmethyl-4-pyrazolyl)ethanol (1.42 g).

Workup

  1. additionTo the solution were added
  2. stirringThe mixture was stirred at 25° C. for one hour
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with an aqueous saline solution, which
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 300 g, developing solvent: ethyl acetate-hexane, 1:1)

Sources & evidence

ORD record
ord-5eb0e8ee898c4b9293039966ec2b7b64
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06174877B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes