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Diethyl Ether → {1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-methanol

HRID 536559
Notes
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Reaction equation

HRID 536559 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.[OH-].[Na+]>C1COCC1>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[C:13]([CH:18]=1)[CH2:12][N:8]1[C:9]([CH3:11])=[CH:10][C:6]([CH2:4][OH:3])=[N:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 686409611-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 68641874{1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester 3 (0.3 g, 0.72 mmol) in THF (6 mL) under N2 atmosphere was added 1M LiAlH4 in Et2O (2.2 mL, 2.20 mmol). The resulting mixture was stirred at RT for 2 h. 2 M NaOH (2 mL) was added dropwise and the precipitate was removed by filtration. The volatiles were removed in vacuo. The residue was dissolved in EtOAc (20 mL), washed with water (2×15 mL), brine (15 mL), dried (Na2SO4) and evaporated to dryness to give alcohol 4 as a white solid, 0.16 g (60%).

Workup

  1. customthe precipitate was removed by filtration
  2. customThe volatiles were removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (20 mL)
  4. washwashed with water (2×15 mL), brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-189888ffda4f4d958a1689fdff1665c2
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859606B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes