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

HRID 453323
Notes
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Reaction equation

HRID 453323 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH:12]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][CH:14]=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][CH:14]=[C:13]([CH:18]=1)[CH:12]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[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 866672831-[5-Chloro-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 86667284{1-[5-Chloro-(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-df7628d62bd2412287ab045f8e841de8
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492424B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes