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Ethanol → 3-(7-Chloroquinol-2-ylmethoxy)benzyl alcohol

HRID 258465
Notes
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Reaction equation

HRID 258465 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:9]2)=[CH:4][CH:3]=1.CCO.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:17][OH:18])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 190028993-((7-Chloro-2-quinolinyl)methoxy)benzaldehyde

Product 1

HCID 197372403-(7-Chloroquinol-2-ylmethoxy)benzyl alcoholYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The aldehyde of Step 1 (46.64 g, 156.6 mmol) was dissolved in 300 mL of THF. At 0° C., 800 mL of EtOH was added, followed by NaBH4 (5.93 g, 157 mmol). The mixture was then stirred at r.t. (room temperature) for 1 h and poured into cold 25% aq (aqueous) NH4OAc. The organic solvents were evaporated and the title alcohol was extracted with toluene:THF 1:1, dried over Na2SO4 and filtered through silica to yield 47.9 g of the title compound.

Workup

  1. customThe organic solvents were evaporated
  2. extractionthe title alcohol was extracted with toluene:THF 1:1
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through silica

Sources & evidence

ORD record
ord-c1f2efb795f7473f9cc6fe029ed93581
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05266568

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes