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

HRID 1053979
Notes
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Reaction equation

HRID 1053979 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 1 M 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-9e92de7049bb4bc3939b3f569dc92faf
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394284B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes