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Sodium hydride → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzaldehyde

HRID 892177
Notes
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Reaction equation

HRID 892177 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=1.[H-].[Na+].F[C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:25]=1[CH:26]=[O:27]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[CH2:19][O:20][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:35])[F:34])[C:25]=1[CH:26]=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5219332-Fluoro-6-(trifluoromethyl)benzaldehydeHCID 14650410Benzenemethanol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 222415012-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

[3-(Quinolin-2-ylmethoxy)-phenyl]-methanol (300 mg, 1.13 mmol, example 48) is dissolved in DMF (6 mL) and sodium hydride (60%, 60 mg, 1.5 mmol) is added and allowed to stir 20 min. 2-Fluoro-6-(trifluoromethyl)benzaldehyde (0.30 mL, 2.2 mmol) is added and the reaction is heated at 90° C. for 5 h. The reaction is partitioned between ethyl acetate (200 mL) and water (200 mL), dried over magnesium sulfate, filtered, concentrated in vacuo and purified by column chromatography (silica, 25% ethyl acetate in hexanes) to provide the title compound; MS (ESI) 438 (M+H)+.

Workup

  1. customThe reaction is partitioned between ethyl acetate (200 mL) and water (200 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (silica, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9e609fead1a744eba16d506ba04f7f74
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07005440B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes